Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]([C:4]1[CH:13]=[CH:12][C:7]([CH2:8][N:9]=[N+:10]=[N-:11])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl.O>[CH2:25]([O:24][C:22]([NH:3][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]=[N+:10]=[N-:11])=[CH:12][CH:13]=1)=[NH:2])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
Reactant: [N-]=[N+]=NCc1ccc(C(=N)N)cc1
Reactant: O=C(Cl)OCc1ccccc1
Agent: Cl
Agent: O=S(=O)([O-])[O-]
Agent: [Mg+2]
Solvent: ClCCl
Solvent: CCN(CC)CC
Solvent: O
Product: [N-]=[N+]=NCc1ccc(C(=N)NC(=O)OCc2ccccc2)cc1
Reaction time: 0.5 h

Procedure:
The crystals from (ii) above were dissolved in 500 ml methylene chloride and the resulting solution was dried (K2CO3), filtered and 27 ml (194 mmol) triethyl amine was added. 25 ml Benzyl chloroformate was slowly added to the stirred solution while the reaction mixture was cooled in an ice bath. After 30 minutes an additional 2 ml benzyl chloroformate was added and stirring was continued for another 30 minutes. Subsequently water was added and the aqueous phase was adjusted to pH 7 with 2M HCl. The organic phase was dries (MgSO4) and the solvent was removed in vacuo. 4-(benzyloxycarbonylamidino) benzyl azide was finally isolated as colorless crystals from ether/methylene chloride/hexane.
Reaction SMILES: Cl[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.Cl.[NH2:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1.[OH-].[NH4+]>O>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[NH:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1
Reactant: NCCc1nc(-c2ccccc2)cs1
Reactant: Fc1cccc2c(Cl)ccnc12
Agent: Cl
Agent: [NH4+]
Agent: [OH-]
Solvent: O
Product: Fc1cccc2c(NCCc3nc(-c4ccccc4)cs3)ccnc12
Yield: 21.3 %

Procedure:
To 1.0 g of 4-chloro-8-fluoroquinoline was added 2.6 g of 2-β-aminoethyl-4-phenylthiazole monohydrochloride. The mixture was stirred under nitrogen and heated to 170°-175° C. for one hour. The mixture was then cooled and 250 mL of a 50:50 mixture of ammonium hydroxide and water was added. The product was extracted into CH2Cl2, which was then concentrated to dryness. Recrystallizing from pentane/CH2Cl2 gave 0.410 g of the title product. Yield 21.6%. M.P. 134°-135° C.
Reaction SMILES: [CH3:1][C@@:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.C(O)C.[OH-].[Li+].O>>[NH2:3][C@@:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]
Reactant: C[C@@]1(c2ccc3cc(Oc4cccc(C(F)(F)F)c4)ccc3c2)COC(=O)N1
Agent: [Li+]
Agent: [OH-]
Solvent: CCO
Solvent: O
Product: C[C@](N)(CO)c1ccc2cc(Oc3cccc(C(F)(F)F)c3)ccc2c1
Temperature: 80 °C
Yield: 53.2 %

Procedure:
(R)-4-Methyl-4-(6-(3-(trifluoromethyl)phenoxy)naphthalen-2-yl)oxazolidin-2-one (20.0 mg, 0.000052 mol) was dissolved in ethanol (2 mL, 0.03 mol), followed by 4 M of lithium hydroxide in water (1 mL, 0.004 mol). The reaction mixture was then heated at 80° C. for 5 hours. All solvent was removed. The solid was extracted with DCM, and was purified via HPLC to give the desired product (10 mg, 52%). 1H NMR (MeOD) δ: 7.91-8.00 (m, 2H), 7.77 (d, J=8.8 Hz, 1H), 7.64 (dd, J=8.8, 1.8 Hz, 1H), 7.51-7.58 (m, 1H), 7.35-7.44 (m, 2H), 7.22-7.30 (m, 3H), 3.64-3.78 (m, 2H), 1.52 (s, 3H). MS (M+1): 362.0
Reaction SMILES: Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[CH:29][NH:30]2)=[CH:26][C:25]=1[OH:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[CH:29][NH:30]2)=[CH:26][C:25]=1[O:33][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1
Reactant: Oc1cc2cc[nH]c2cc1F
Reactant: COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CN(C)C=O
Product: COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCC1CCN(C)CC1
Temperature: 95 °C
Reaction time: 3.5 h
Yield: 46.7 %

Procedure:
A solution of 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (213 mg, 0.662 mmol), (prepared as described for the starting material in Example 10), and 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol) in DMF (3 ml) containing potassium carbonate (137 mg, 0.994 mmol) was stirred at 95° C. for 3.5 hours. After cooling, the mixture was poured onto water. The mixture was filtered and the solid was washed with water. The solid was dissolved in methylene chloride. The organic layer was dried (MgSO4), and evaporated. The residue was triturated with ether/ethyl acetate and the solid was filtered and dried under vacuum to give 4-(6-fluoroindol-5-yloxy)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (135 mg, 46%).
Reaction SMILES: [CH:1]1([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]([O:27]CC)=[O:26])[CH2:21][CH2:20]2)[CH:12]=[CH:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([CH2:18][N:19]2[CH2:20][CH2:21][CH:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]2)[CH:12]=[CH:11]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
Reactant: CCOC(=O)C1CCN(Cc2ccc3cc(OC4CCCCC4)ccc3n2)CC1
Agent: [Na+]
Agent: [OH-]
Solvent: CCO
Product: O=C(O)C1CCN(Cc2ccc3cc(OC4CCCCC4)ccc3n2)CC1
Yield: 36.2 %

Procedure:
Ethyl 1-((6-(cyclohexyloxy)quinolin-2-yl)methyl)piperidine-4-carboxylate (117 mg, 0.30 mmol) was dissolved in EtOH (5 mL). NaOH (24 mg, 0.60 mmol, 2 eq) was added in one portion at room temperature. The mixture was stirred at reflux for 2 h. The solvent was removed and the residue was dissolved in H2O (3 mL) and adjusted to pH=7 with HCl (1 M). The precipitate was collected and dried under vacuum to give 1-((6-(cyclohexyloxy)quinolin-2-yl)methyl)piperidine-4-carboxylic acid (40 mg, yield: 58%) as white solid. ESI-MS (M+H)+: 369.2, HPLC: 97.89%. 1H NMR (400 MHz, CD3OD) δ: 8.18 (d, J=8.8 Hz, 1H), 7.89 (d, J=9.2 Hz, 1H), 7.37 (d, J=8.4 Hz, 1H), 7.33 (dd, J=8.8, 2.4 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 4.51 (s, 2H), 4.45-4.40 (m, 1H), 3.56-3.52 (m, 2H), 3.23-3.20 (m, 2H), 2.65-2.62 (m, 1H), 2.16-2.11 (m, 2H), 2.00-1.93 (m, 4H), 1.75-1.71 (m, 2H), 1.53-1.23 (m, 6H).
Reaction SMILES: Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1>O1CCCC1>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:7]=1
Reactant: c1c[nH]cn1
Reactant: Clc1cc(Cl)ncn1
Solvent: C1CCOC1
Product: Clc1cc(-n2ccnc2)ncn1
Yield: 78.4 %

Procedure:
In anhydrous tetrahydrofuran, 298 mg of 4,6-dichloro-pyrimidine was substituted with 136 mg of imidazole. The reaction mixture was treated according to the procedure of Example 5 to yield 283 mg of the 6-chloro-4-(1-imidazolyl)pyrimidine, recrystallized from a mixture of n-hexane and ethyl acetate, having a melting point of 131.5°-132° C.
Reaction SMILES: [S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=1.[OH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.N1CCCCC1>C(O)C>[OH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[C:10]1[C:9]2[C:13](=[CH:14][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH:8]=2)[NH:12][C:11]1=[O:15]
Reactant: O=C1Cc2ccc(-c3cccs3)cc2N1
Reactant: O=Cc1ccccc1O
Solvent: CCO
Solvent: C1CCNCC1
Product: O=C1Nc2cc(-c3cccs3)ccc2C1=Cc1ccccc1O
Yield: 50.1 %

Procedure:
A mixture of 6-thiophen-2-yl-1,3-dihydroindol-2-one (100 mg, 0.5 mmol), 2-hydroxybenzaldehyde (60 mg, 0.5 mmol) and piperidine (0.23 mL) in ethanol (4 mL) was stirred at reflux overnight. The reaction mixture was concentrated and column chromatographed (eluant—isopropanol/dichloromethane) to give 80 mg (50%) of 3-(2-hydroxybenzylidene)-6-thiophen-2-yl-1,3-dihydroindol-2-one as a yellow-orange solid.
Reaction SMILES: Br[C:2]1[C:3]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:4]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[C:5](=[O:20])[N:6]([CH2:8][C:9]2[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[N:7]=1.[NH2:36][NH2:37]>N1C=CC=CC=1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:3]2[C:2]([NH:36][NH2:37])=[N:7][N:6]([CH2:8][C:9]3[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=3)[C:5](=[O:20])[C:4]=2[C:21]2[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=2)=[CH:30][CH:31]=1
Reactant: Cc1nc(C(F)(F)F)ccc1Cn1nc(Br)c(-c2ccc(Cl)cc2)c(-c2ccc(C#N)cc2)c1=O
Reactant: NN
Solvent: c1ccncc1
Product: Cc1nc(C(F)(F)F)ccc1Cn1nc(NN)c(-c2ccc(Cl)cc2)c(-c2ccc(C#N)cc2)c1=O
Reaction time: 0.5 h

Procedure:
To a microwave flask was added 4-(6-bromo-5-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (105 mg, 0.187 mmol), pyridine (10 ml) and anhydrous hydrazine (60 mg, 1.87 mmol). The reaction was subjected to microwave at 200° C. for 30 min. After this time the solvent was removed to give 4-(5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile as a yellow solid. The material was used in the next step without further purification.
Reaction SMILES: [Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:29])[C@@H:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1
Reactant: COCCC[C@H]1CN(C2=Nc3cc(Cl)ccc3Nc3sccc32)CCN1
Reactant: CC(=O)O[BH-](OC(C)=O)OC(C)=O
Agent: C=O
Agent: [Na+]
Solvent: ClCCl
Product: COCCC[C@H]1CN(C2=Nc3cc(Cl)ccc3Nc3sccc32)CCN1C
Temperature: 25 °C
Reaction time: 0.08 h
Yield: 76.5 %

Procedure:
Combine (S)-7-chloro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene (280.3 mg, 0.72 mmol), formaldehyde (64.0 μL, 0.79 mmol, 37% in water), and dichloromethane (10.0 ml). Stir the mixture at ambient temperature for 5 minutes and then add sodium triacetoxyborohydride (227.9 mg, 1.08 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion and wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10) to give 223.0 mg (77%) of the title compound: mass spectrum (ion spray): m/z=405.1 (M+1).
Reaction SMILES: [Cl:1][C:2]1[C:3]2[C:4]3[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][C:10]=1[CH3:11].ClC1C(C)=CC2C3CN(C)CCC=3NC=2C=1.[H-].[Na+].[CH3:35][C:36]1([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)[CH2:38][O:37]1>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:4]3[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][C:5]=3[N:6]([CH2:35][C:36]([C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)([OH:37])[CH3:38])[C:7]=2[CH:8]=[CH:9][C:10]=1[CH3:11]
Reactant: CC1(c2cccnc2)CO1
Reactant: Cc1ccc2[nH]c3c(c2c1Cl)CN(C)CC3
Agent: Cc1cc2c3c([nH]c2cc1Cl)CCN(C)C3
Agent: [H-]
Agent: [Na+]
Solvent: CN(C)C=O
Product: Cc1ccc2c(c1Cl)c1c(n2CC(C)(O)c2cccnc2)CCN(C)C1
Reaction time: 0.25 h

Procedure:
A mixture of 9-chloro-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole and 7-chloro-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.00 g, 8.5 mmol) was dissolved in DMF (15 mL). Sodium hydride (1.708 g, 42.71 mmol) was added at 0-10° C. and stirred at the same temperature for 15 min., 3-(2-methyloxiran-2-yl)pyridine (2.309 g, 17.08 mmol) was added dropwise into the reaction mixture and the mixture was stirred at RT for 16 h. The reaction was monitored by TLC and LCMS. After consumption of starting material, the reaction mixture was quenched with ice cold water (100 mL) and extract with EtOAc (300 mL). The organic layer was washed with water (5×100 mL). The organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude. The crude product was purified by reverse phase column chromatography to obtain 35 mg of 1-(9-chloro-2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-3-yl)propan-2-ol. 1H NMR (CD3OD, freebase) δ (ppm): 8.46 (s, 1H), 8.34 (d, 1H), 7.82 (d, 1H), 7.29 (t, 1H), 6.87 (d, 1H), 6.77 (d, 1H), 4.22 (dd, 2H), 3.99 (q, 2H), 2.73 (m, 4H), 2.5 (s, 3H), 2.3 (s, 3H), 1.66 (s, 3H). Separation by chiral HPLC provided enantiomers II-124a-b.
Reaction SMILES: C1(CN[C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[N:8]=[CH:9][N:10]3[C@H]2CC[C@@H](CO)O2)CC1.C(N(CC)CC)C.C1(CC(Cl)=O)C=CC=CC=1>C(#N)C.CN(C)C1C=CN=CC=1>[N:14]1[CH:6]=[C:7]2[C:11]([NH:10][CH:9]=[N:8]2)=[N:12][CH:13]=1
Reactant: OC[C@@H]1CC[C@H](n2cnc3c(NCC4CC4)ncnc32)O1
Agent: CN(C)c1ccncc1
Agent: O=C(Cl)Cc1ccccc1
Solvent: CC#N
Solvent: CCN(CC)CC
Product: c1ncc2nc[nH]c2n1
Temperature: 25 °C
Reaction time: 0.5 h
Yield: 78 %

Procedure:
6-(Cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl]-9H-purine (0.5 g, 1.44 mmoles) was dissolved in 20 mL acetonitrile. 4-Dimethylaminopyridine (10.2 mg, 0.08 mmoles) and triethylamine (620 μL, 4.4 mmoles) were added and the flask was chilled in an ice bath under a nitrogen atmosphere. Phenylacetyl chloride (1.11 g, 7.2 mmoles, Aldrich Chemical Co., Madison, WI) was added dropwise to the flask over a period of 15 minutes. The reaction was stirred at room temperature for 0.5 hours. The reaction was quenched with methanol and solvents were removed under vacuo. The residue was dissolved in 2 mL CHCL3 /CH3OH (9:1) and chromatographed on a column of silica gel (5×15 cm) in the application solvent. Additional chromatography was performed on the product containing fractions using a Chromatotron 2 mm silica gel plate developed with a hexane:acetone mixture (7:3). Lyophilization of the product containing fractions afforded 0.459 g of 6 -(cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-[(phenylacetyl)methyl]-2-furyl)]-9H-purine as an oil (78% yield): m.p. <25° C.
Reaction SMILES: [Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH:29]1([C:32]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=O)[CH2:31][CH2:30]1>CCOCC>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]([CH:29]2[CH2:31][CH2:30]2)=[CH:2][O:3][CH3:4])=[CH:35][CH:36]=1
Reactant: COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1
Reactant: O=C(c1ccc(Cl)cc1)C1CC1
Agent: [Cl-]
Agent: [Li]CCCC
Solvent: CCOCC
Product: COC=C(c1ccc(Cl)cc1)C1CC1
Temperature: 2.5 °C
Reaction time: 1.5 h
Yield: 59.4 %

Procedure:
A solution of methoxymethyl triphenyl phosphonium chloride (20.5 g, 0.060 mol) in ether is cooled to −60° C., treated with a 2.5 M solution of butyllithium in hexanes (25.2 mL, 0.063 mol), warmed to and stirred at 0-5° C. for 90 minutes, recooled to −60° C., treated with a solution of 4-chlorophenyl cyclopropyl ketone (9.03 g, 0.050 mol) in ether, warmed to and stirred at room temperature overnight, quenched with ethyl acetate and 2 N hydrochloric acid, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2 N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:9) gives the title product as an oil (6.2 g, 60%).
Reaction SMILES: [C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(O)[CH:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl>[C:24]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
Reactant: COC(=O)C(Cc1ccc2c(c1)OCO2)C(O)(c1ccccc1)c1ccccc1
Agent: Cl
Product: COC(=O)C(Cc1ccc2c(c1)OCO2)=C(c1ccccc1)c1ccccc1
Yield: 23.5 %

Procedure:
Methyl (2RS)-3,3-diphenyl-3-hydroxy-2-(3,4-methylenedioxybenzyl)propanoate (0.309 g, 0.79 mmol) was dissolved in methanolic HCl (60 ml) (prepared by passing HCl gas through MeOH at 0° C.). After 4 days at ambient temperature the MeOH was removed by evaporation and replaced with fresh methanolic HCl. After a further 2 days the methanol was evaporated. The residue was recrystallized (MeOH) to give the title compound as a colorless solid (69 mg, 23%).