Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[C:13]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]>C(O)CCCC>[C:13]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:4]3[N:3]=[C:2]([NH2:1])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([CH3:16])([CH3:14])[CH3:15]
Reactant: Nc1nc(Cl)nc2ccccc12
Reactant: CC(C)(C)OC(=O)c1ccc(NC2CCNCC2)cc1
Solvent: CCCCCO
Product: CC(C)(C)OC(=O)c1ccc(NC2CCN(c3nc(N)c4ccccc4n3)CC2)cc1
Temperature: 120 °C
Yield: 73.3 %

Procedure:
4-amino-2-chloro-quinazoline (0.070 g, 0.39 mmol) was added to a solution of (49) (0.13 g, 0.47 mmol) in n-pentanol (5 mL) at 25° C. The mixture was heated to 120° C. and was maintained at that temperature for 12 h. The reaction mixture was then cooled to room temperature and concentrated to a brown yellow oily residue. Purification of the residue by flash column chromatography (gradient elution 0 to 5% MeOH in CH2Cl2) provided the title compound (0.12 g, 73%): TLC (Rf =0.33; 5% MeOH/CH2Cl2); 1H NMR (CDCl3) δ 7.83 (d, 2H, J=8.7), 7.51 (m, 3H), 7.10 (t, 1H, J=6.6), 6.57 (d, 2H, J=8.8), 5.35 (br s, 2H), 4.81 (d, 2H, J=13.6), 4.00 (br s, 1H), 3.60 (m, 1H), 3.14 (t, 2H, J=14.0), 2.13 (d, 2H, J=13.2), 1.57 (s, 9H), 1.47 (m, 2H); 13C NMR (CDCl3) δ 166.1, 161.6, 158.8, 152.0, 150.4, 133.2, 131.5, 125.9, 121.8, 121.3, 120.3, 111.8, 109.7, 79.9, 50.3, 42.8, 32.3, 28.3; Anal. (C24H29N5O2 ·1/4HCl)·C, H, N.
Reaction SMILES: I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.[CH3:33][O:34][CH:35]([CH3:40])[CH2:36][CH2:37][CH:38]=[O:39]>>[CH3:33][O:34][CH:35]([CH3:40])[CH2:36][CH2:37][C:38]([C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[NH:4][CH:3]=1)=[O:39]
Reactant: COC(C)CCC=O
Reactant: COc1cc(-c2cnc3c(n2)c(I)cn3[Si](C(C)C)(C(C)C)C(C)C)cc(OC)c1OC
Product: COc1cc(-c2cnc3[nH]cc(C(=O)CCC(C)OC)c3n2)cc(OC)c1OC

Procedure:
4-Methoxy-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pentan-1-one was prepared starting from 7-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine and 4-methoxy-pentanal (Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1919), 52B 1800-12) following general procedures as described in these Examples 66, to afford a brown solid. MP 150-151° C., M+H=400.
Reaction SMILES: C([O:4][C@@H:5]1[C@@H:32]([O:33]C(=O)C)[C@H:31]([O:37]C(=O)C)[C@@H:30]([CH2:41][O:42]C(=O)C)[O:29][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=1)(=O)C.[OH-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=1)[C@@H:6]1[O:29][C@H:30]([CH2:41][OH:42])[C@@H:31]([OH:37])[C@H:32]([OH:33])[C@H:5]1[OH:4]
Reactant: COCOCCc1ccc(Cc2ccc(OC)cc2O[C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1
Agent: [Na+]
Agent: [OH-]
Solvent: CO
Product: COCOCCc1ccc(Cc2ccc(OC)cc2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1
Temperature: 25 °C
Reaction time: 0.42 h
Yield: 55.5 %

Procedure:
To a solution of 5-methoxy-2-{4-[2-(methoxymethyloxy)ethyl]benzyl}phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.13 g) in methanol (8 mL) was added 2 mol/L sodium hydroxide (0.50 mL), and the mixture was stirred at room temperature for 25 minutes. The solvent was removed under reduced pressure, and the residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=7/1) to give 5-methoxy-2-{4-[2-(methoxymethyloxy)ethyl]benzyl}phenyl β-D-glucopyranoside (0.053 g).
Reaction SMILES: [Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[C:11]([F:17])=[N:12][CH:13]=[C:14]([CH3:16])[CH:15]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][C:10]1[C:11]([F:17])=[N:12][CH:13]=[C:14]([CH2:16][Br:1])[CH:15]=1
Reactant: O=C1CCC(=O)N1Br
Reactant: Cc1cnc(F)c(Br)c1
Agent: O=C(OOC(=O)c1ccccc1)c1ccccc1
Solvent: ClC(Cl)(Cl)Cl
Product: Fc1ncc(CBr)cc1Br
Yield: 22.3 %

Procedure:
N-Bromosuccinimide (4.732 g, 26.59 mmol) and benzoyl peroxide (0.1356 g, 0.5598 mmol) were added to a solution of 3-bromo-2-fluoro-5-methylpyridine (Matrix Innovation Inc., Montreal, Quebec, Canada 5.318 g, 27.99 mmol) in CCl4 (50 mL), and the mixture was heated at gentle reflux under a N2 atmosphere for 16 h. The mixture was filtered, washing with CCl4, and the residue concentrated and purified by flash chromatography on silica (1% to 1.5% EtOAc/hexane) to give 3-bromo-5-(bromomethyl)-2-fluoropyridine (1.593 g, 21.17% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H); 8.03 (dd, J=8.02, 2.15 Hz, 1H); 4.43 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −65.17 (br. s., 1 F). Sample did not ionize well in ESI+ mode.
Reaction SMILES: [N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[C:7]([O:9][CH3:10])=[O:8].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(#N)C>[CH2:24]([N:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1)[C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1
Reactant: BrCc1ccccc1
Reactant: COC(=O)C1CNCCN1C(=O)OC(C)(C)C
Solvent: CC#N
Solvent: CCN(CC)CC
Product: COC(=O)C1CN(Cc2ccccc2)CCN1C(=O)OC(C)(C)C
Temperature: 71 °C
Yield: 65.6 %

Procedure:
To a dry 100 ml one necked round bottom flask equipped with a stirring bar was added 1-tert-butyl 2-methyl piperazine-1,2-dicarboxylate (5 g, 20.5 mmol) under N2 (FIG. 1). Anhydrous acetonitrile (60 mL) was added followed by the additions of BnBr (2.7 mL, 22.5 mmol) and triethylamine (8.5 ml, 61.5 mmol). A condenser was then put on to the flask and the reaction mixture was heated at 71° C. for 45 minutes. The reaction mixture was allowed to come to room temperature and concentrated under reduced pressure. It was then diluted with dicholoromethane and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified with flash column (PE:EA=8:1) to yield 4.5 g (66%) of 111a. MS: [M+H]+: 335
Reaction SMILES: [Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:20]=2[CH3:31])(=[O:18])=[O:17])[C:12]([OH:14])=O)=[O:8])=[CH:4][CH:3]=1.[CH:32]1([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:34][CH2:33]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[ClH:1].[ClH:1].[CH:32]1([N:35]2[CH2:40][CH2:39][N:38]([C:12](=[O:14])[C@@H:11]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[C:20]=3[CH3:31])(=[O:17])=[O:18])[CH2:10][NH:9][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:8])[CH2:37][CH2:36]2)[CH2:34][CH2:33]1
Reactant: Cc1c(-c2cccnc2)cccc1S(=O)(=O)N[C@@H](CNC(=O)c1ccc(Cl)s1)C(=O)O
Reactant: C1CN(C2CC2)CCN1
Agent: CN(C)C(On1nnc2ccccc21)=[N+](C)C
Agent: F[B-](F)(F)F
Solvent: CCN(C(C)C)C(C)C
Solvent: ClCCl
Product: Cc1c(-c2cccnc2)cccc1S(=O)(=O)N[C@@H](CNC(=O)c1ccc(Cl)s1)C(=O)N1CCN(C2CC2)CC1
Product: Cl
Temperature: 25 °C
Reaction time: 1 h

Procedure:
Intermediate 78 (202 mg, 0.42 mmol) was dissolved in 10 ml DCM and N-cyclopropyl piperazine (105 mg, 0.84 mmol) was added followed by DIPEA (0.29 ml, 1.68 mmol) and TBTU (202 mg, 0.63 mmol). After stirring for 1 h at RT the solution was evaporated to dryness and purified by silica gel chromatography (Elution with DCM/methanol from 0 to 10% of methanol). The solid obtained after evaporation of the solvents was dissolved in DCM, HCl 2M in Et2O (5 ml) was added and the solvents were evaporated. Yield: 163 mg, 59%. MS (ES+): m/e=588.
Reaction SMILES: [C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[OH:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[CH2:23][NH2:24]>C(OCC)(=O)C.C1CCCCC1>[ClH:31].[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:24][CH2:23][CH:22]([O:21][CH2:20][CH2:19][CH2:18][OH:17])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]
Reactant: NCC(OCCCO)c1cccc(Cl)c1
Reactant: COC(=O)COc1ccc(CC(C)=O)cc1
Solvent: C1CCCCC1
Solvent: CCOC(C)=O
Product: COC(=O)COc1ccc(CC(C)NCC(OCCCO)c2cccc(Cl)c2)cc1
Product: Cl

Procedure:
The title compound was prepared as a 56:44 mixture of diastereoisomers, mp 110°-114° C. (ethyl acetate-cyclohexane), from 1-(4-carbomethoxymethoxyphenyl)propan-2-one (4.3 g) and 2-(3-hydroxypropoxy)-2-(3-chlorophenyl)ethanamine (4.5 g) by an analogous procedure to that described in Example 1.
Reaction SMILES: [OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][C:4](=[O:14])[C:3]=1[C:15](=O)[CH2:16][CH2:17][CH3:18].Cl.[CH2:21]([O:23][NH2:24])[CH3:22].O.O.O.C([O-])(=O)C.[Na+].C(O)(=O)C>C(O)C>[CH2:21]([O:23][N:24]=[C:15]([C:3]1[C:4](=[O:14])[CH2:5][CH:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][C:2]=1[OH:1])[CH2:16][CH2:17][CH3:18])[CH3:22]
Reactant: CCCC(=O)C1=C(O)CC(c2cccnc2)CC1=O
Reactant: CCON
Agent: CC(=O)[O-]
Agent: Cl
Agent: [Na+]
Solvent: CCO
Solvent: CC(=O)O
Solvent: O
Product: CCCC(=NOCC)C1=C(O)CC(c2cccnc2)CC1=O

Procedure:
3-Hydroxy-5-(3-pyridyl)-2-butyrylcyclohex-2-en-1-one (1.0 g) was stirred with O-ethylhydroxylamine hydrochloride (1.1 equiv) and sodium acetate trihydrate (1.1 equiv) in ethanol (30 ml) at room temperature for 12 hr. The mixture was poured into a dilute acetic acid solution, which was subsequently extracted with ether. The dried (MgSO4) organic extract was evaporated to give 2-[1-(ethoxyimino)-butyl]-3-hydroxy-5-(3-pyridyl)cyclohex-2-en-1-one as an oil.
Reaction SMILES: [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=2[O:33][CH3:34])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:35])[NH:17]2)(=[O:11])=[O:10].[Cl:36]N1C(=O)CCC1=O>CN(C)C=O>[Cl:36][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:21]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=3[O:33][CH3:34])[C:13]=2[NH:12][S:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])(=[O:11])=[O:10])[NH:17][C:16]=1[CH3:35]
Reactant: COc1cc(CC(=O)O)ccc1Oc1ccc2[nH]c(C)cc2c1NS(=O)(=O)c1ccc(Cl)cc1Cl
Reactant: O=C1CCC(=O)N1Cl
Solvent: CN(C)C=O
Product: COc1cc(CC(=O)O)ccc1Oc1ccc2[nH]c(C)c(Cl)c2c1NS(=O)(=O)c1ccc(Cl)cc1Cl
Reaction time: 0.67 h

Procedure:
A room temperature solution of 1 (14 mg, 0.026 mmol) and N-chlorosuccinimide (4 mg, 0.029 mmol) dissolved in N,N-dimethylformamide (1 mL) was stirred for 40 min., after which time HPLC indicated no 1 remained. The reaction was partitioned between ethyl acetate and 10% sodium thiosulfate aqueous solution. The organic separation was washed twice with water then brine. The organic layer was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a colorless solid. The product was isolated by semi-preparative reversed phase HPLC to afford a colorless solid. LC-MS ESI (neg.) m/z: 567.1 (M−H). 1H NMR (400 MHz) (d6-DMSO) δ 11.41 (s, 1H); 9.66 (br s, 1H); 7.64 (d, J=8 Hz, 1H); 7.52 (s, 1H); 7.18 (d, J=8.0 Hz, 1H); 6.86 (s, 1H); 6.61 (d, J=8.0 Hz, 1H); 6.35 (d, J=8.0 Hz, 1H); 6.23 (d, J=8.0 Hz, 1H); 3.66 (s, 3H); 3.51 (s, 2H); 2.38 (s, 3H) ppm.
Reaction SMILES: [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH:14]=O.[NH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[N:18]1([CH:14]([NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:13][C:12]([CH3:17])([CH3:16])[CH3:11])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1
Reactant: CC(C)(C)CC=O
Reactant: NC(=O)c1ccc(Br)cc1
Reactant: c1ccc2[nH]nnc2c1
Agent: Cc1ccc(S(=O)(=O)O)cc1
Product: CC(C)(C)CC(NC(=O)c1ccc(Br)cc1)n1nnc2ccccc21

Procedure:
A suspension of 4-bromobenzamide, 3,3-dimethylbutanal, benzotriazole, and p-toluenesulfonic acid was processed as described in Example 53A to provide the desired product.
Reaction SMILES: [CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[N:16]=2)[CH2:11][C:12](O)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:31][OH:32]>O1CCCC1>[NH3:16].[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)(=[O:23])=[O:22])[N:16]=2)[CH2:11][C:12]([NH:31][OH:32])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
Reactant: NO
Reactant: O=C(O)C[C@@H](CCCC1CCCCC1)c1nc(CS(=O)(=O)c2ccccc2)no1
Agent: Cl
Solvent: C1CCOC1
Product: N
Product: O=C(C[C@@H](CCCC1CCCCC1)c1nc(CS(=O)(=O)c2ccccc2)no1)NO
Temperature: 25 °C
Reaction time: 2 h
Yield: 49.2 %

Procedure:
A solution of (3R)-6-cyclohexyl-3-{3-[(phenylsulfonyl)methyl]-1,2,4-oxadiazol-5-yl}hexanoic acid (Preparation 55) (60 mg, 0.14 mmol) in anhydrous tetrahydrofuran (4 ml) was treated with 1,1′-(25 mg, 0.15 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 2 hours. Hydroxylamine hydrochloride (10 mg, 0.14 mmol) was then added and the mixture was stirred for 18 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (95:5:0.5) to afford the title compound as an oil (15 mg).
Reaction SMILES: [C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:3][CH:2]=1.[C:18]([O-:21])([O-:20])=O.[Na+].[Na+].BrBr.[CH:26]1C=CC=CC=1>CO.CCOC(C)=O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]([O:9][CH3:10])[O:20][CH:18]([O:21][CH3:26])[CH:11]=2)=[CH:3][CH:2]=1
Reactant: O=C([O-])[O-]
Reactant: c1ccccc1
Reactant: c1ccc(-c2ccc(-c3ccoc3)cc2)cc1
Agent: BrBr
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: CO
Product: COC1C=C(c2ccc(-c3ccccc3)cc2)C(OC)O1
Reaction time: 0.5 h
Yield: 74 %

Procedure:
To a slurry of 3-(biphenyl-4-yl)furan (100 mg, 0.450 mmol) and Na2CO3 (48 mg, 0.45 mmol) in benzene (1 mL) and MeOH (1 mL) at −10° C. was added bromine (22 μL, 0.43 mmol) dropwise via syringe. After 30 minutes at −10° C., the mixture was diluted with EtOAc and filtered twice. The filtrate was concentrated to give a crude solid which was purified via flash column chromatography with a 0-1% EtOAc/CH2Cl2 gradient eluant to provide 90 mg (74%) of a diasteromeric mixture of 3-(biphenyl-4-yl)-2,5-dihydro-2,5-dimethoxyfuran as a colorless oil.