Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:15])[CH2:10][CH2:11][C:12]([OH:14])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH3:30][C@@H:31]1[C@H:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:34][C:33](=[O:42])[NH:32]1.[Cl-].[Li+]>C1COCC1>[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:15])[CH2:10][CH2:11][C:12]([N:32]2[C@H:31]([CH3:30])[C@H:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:34][C:33]2=[O:42])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
Reactant: C[C@@H](CCC(=O)O)CCC1CCCCC1
Reactant: C[C@H]1NC(=O)O[C@H]1c1ccccc1
Agent: CC(C)(C)C(=O)Cl
Agent: [Cl-]
Agent: [Li+]
Solvent: C1CCOC1
Solvent: CCN(CC)CC
Product: C[C@@H](CCC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@H]1C)CCC1CCCCC1
Temperature: 0 °C
Reaction time: 1 h

Procedure:
A flask was charged with 4.17 g (19.6 mmol) of (R)-6-cyclohexyl-4-methyl-hexanoic acid, 40 mL of THF, and 8.56 mL (61.4 mmol) of triethylamine. The mixture was cooled in a 0° C. bath, and 2.41 mL (19.6 mmol) of pivaloyl chloride was added. The mixture was stirred for 1 h at 0° C. Then 2.79 g (16.4 mmol) of (4R,5S)-4-methyl-5-phenyl-2-oxazolidinone and 0.823 g (19.6 mmol) of lithium chloride were added as solids. The mixture was allowed to warm to room temperature and stirred overnight. The resulting solids were filtered off. The solvent was stripped under reduce pressure, and the residue was purified by column chromatography (eluent: 4:1 hexanes/ethyl acetate) to give 6.09 g (quant.) of a clear oil: 1H NMR (400 MHz, CDCl3) δ ppm 0.89 (m, 8 H) 1.16 (m, 6 H) 1.68 (m, 9 H) 2.87 (m, 1 H) 2.99 (m, 1 H) 4.76 (qd, J=6.83, 6.59 Hz, 1 H) 5.66 (d, J=7.32 Hz, 1 H) 7.30 (m, 2 H) 7.40 (m, 3 H). MS (APCl) m+1/z=372.
Reaction SMILES: [CH2:1]([NH2:4])[CH2:2][CH3:3].[CH2:5]([N:9]=[C:10]=[O:11])[CH2:6][CH2:7][CH3:8]>C1(C)C=CC=CC=1>[CH2:1]([NH:4][C:10]([NH:9][CH2:5][CH2:6][CH2:7][CH3:8])=[O:11])[CH2:2][CH3:3]
Reactant: CCCN
Reactant: CCCCN=C=O
Solvent: Cc1ccccc1
Product: CCCCNC(=O)NCCC
Yield: 96.1 %

Procedure:
205.76 Grams (3.48 moles) of n-propylamine were charged to a 1--1., round bottom flask equipped with stirrer, thermometer, reflux condenser and addition funnel. 313.7 Grams (3.16 moles) of butyl isocyanate were charged to the addition funnel and added to the flask with stirring at a rate which maintained the contents at about 60°-65° C. Toluene was added to dissolve the solid product for transfer to a stripping vessel. The crude product solution was about 92 area % ureas on a solvent-free basis by gas chromatography. The crude product solution was freed of most of the solvent and lights under vacuum with a rotary evaporator leaving 480.6 g of pale yellow solid melting from 68°-70° C. Infrared analysis showed a clean spectrum in agreement with the proposed structure's functionality. The gas chromatograph showed three, major peaks in a 1:2:1 ratio indicating possible `scrambling` of alkyl groups and a statistically determined ratio of products.
Reaction SMILES: [CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[C:13]([NH2:15])[CH:14]=2)[O:3]1.[C:20]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)(=[O:22])[CH3:21].C(NC1C=CC(C(O)=O)=CC=1)(=O)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:20]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:15][C:13]2[CH:14]=[C:9]([B:4]3[O:3][C:2]([CH3:19])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:10]=[CH:11][C:12]=2[N+:16]([O-:18])=[O:17])=[O:29])=[CH:26][CH:25]=1)(=[O:22])[CH3:21]
Reactant: CC1(C)OB(c2ccc([N+](=O)[O-])c(N)c2)OC1(C)C
Reactant: CC(=O)Nc1ccc(C(=O)Cl)cc1
Agent: CC(=O)Nc1ccc(C(=O)O)cc1
Agent: CN(C)c1ccncc1
Solvent: c1ccncc1
Product: CC(=O)Nc1ccc(C(=O)Nc2cc(B3OC(C)(C)C(C)(C)O3)ccc2[N+](=O)[O-])cc1
Temperature: 25 °C
Reaction time: 16 h
Yield: 16 %

Procedure:
To a solution of compound 132 (18 mg, 0.689 mmol) in pyridine (2.8 mL) was added 4-acetamidobenzoyl chloride (150 mg, 0.758 mmol) and 4-(dimethylamino)pyridine (8 mg, 0.07 mmol) and the mixture was stirred for 16 h. at r.t. Then, it was partitioned between EtOAc and H2O, The aqueous layer was extracted with fresh EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude oil was purified by flash chromatography on silica gel using methanol/EtOAc (5:95) as the eluent affording the title compound 133 (47 mg, 16% yield) as a 1:1 mixture with 4-acetamidobenzoic acid (hydrolyzed starting material). 1H NMR: (Acetone-d6) δ(ppm): 10.76 (bs, 1H), 9.52 (bs, 1H), 9.00 (d, J=1.0 Hz, 1H), 8.20 (d, J=7.2 Hz, 1H), 7.99 (d, J=8.6 Hz, 2H), 7.85 (d, J=8.6 Hz, 2H), 7.64 (dd, J=8.2, 1.2 Hz, 1H), 2.15 (s, 3H), 1.40 (s, 12H).
Reaction SMILES: CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH3:11][C:12]1[NH:13][CH:14]=[C:15]([CH3:26])[C:16]=1[C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.[OH-].[K+]>ClCCl.O.C(OCC)(=O)C.CCCCCC.C(O)(=O)C>[CH:3]([C:14]1[NH:13][C:12]([CH3:11])=[C:16]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[C:15]=1[CH3:26])=[O:4]
Reactant: Cc1c[nH]c(C)c1-c1ccc(C(=O)O)cc1
Reactant: CN(C)C=O
Agent: [K+]
Agent: [OH-]
Solvent: CC(=O)O
Solvent: ClCCl
Solvent: CCCCCC
Product: Cc1[nH]c(C=O)c(C)c1-c1ccc(C(=O)O)cc1
Temperature: 5 °C
Yield: 44.6 %

Procedure:
Dimethylformamide (7.5 g) and 45 mL of dichloromethane were cooled to 6° C. and 7.3 mL of phosphorus oxychloride were added with stirring. 4-(2,4-Dimethyl-1H-pyrrol-3-yl)-benzoic acid (11.1 g) was slowly added. The mixture was refluxed for 30 minutes. Thin layer chromatography (ethyl acetate:hexane:acetic acid 4:6:0.5) showed no starting material at Rf 0.5 and a new spot at the origin. The mixture was cooled to 5° C. and 50 mL of ice water were added. Potassium hydroxide (9 N, 60 mL total) was slowly added with cooling. The final pH was 12–13. The maximum temperature reached was 48° C. Water (100 mL) was added along with 15 mL of dichloromethane, some of which had boiled off. The aqueous phase was isolated at a temperature of about 35° C. to prevent precipitation. The aqueous phase was adjusted to pH 3 by slow addition of about 21 mL of 10 N hydrochloric acid with stirring and cooling in an ice bath. The solids were collected by vacuum filtration and washed 3 times with 15 mL of water each time to give 5.6 g (50% yield) of 4-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-benzoic acid as a tan solid. 1H-NMR (dimethylsulfoxide-d6) δ 2.23, 2.27 (2×s, 2×3H, 2×CH3), 7.40, 7.95 (multiplets, 4H, aromatic), 9.56 (s, 1H, CHO), 11.85 (br s, 1H, NH), 12.90 (br s, 1H, COOH). MS m/z 244 [M+1].
Reaction SMILES: CN(C)CCNC.C([Li])CCC.[CH3:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH:25]=[O:26].[C:27](=[O:29])=[O:28].Cl>O1CCCC1>[OH:26][CH:25]1[O:29][C:27](=[O:28])[C:17]2[CH:18]=[C:19]3[C:24](=[C:15]([O:14][CH3:13])[C:16]1=2)[CH:23]=[CH:22][CH:21]=[CH:20]3
Reactant: O=C=O
Reactant: COc1c(C=O)ccc2ccccc12
Agent: CNCCN(C)C
Agent: Cl
Agent: [Li]CCCC
Solvent: C1CCOC1
Product: COc1c2c(cc3ccccc13)C(=O)OC2O
Temperature: -20 °C
Reaction time: 0.25 h
Yield: 3.7 %

Procedure:
N,N,N′-Trimethylethylene diamine (0.82 ml, 6.3 mmol) was dissolved in tetrahydrofuran (16 ml) and cooled to −20° C. n-Butyl lithium (1.6M in hexanes, 3.9 ml, 6.24 mmol) was added and the reaction stirred at −20° C. for 15 min. 1-Methoxy-2-naphthaldehyde (0.96 g, 5.9 mmol) was added followed by n-butyl lithium (1.6M in hexanes, 11.25 ml, 18 mmol) and the reaction stirred at 25° C. for 3 h. Solid carbon dioxide was added and the reaction left until the excess carbon dioxide had sublimed. Stirring continued for 15 min before addition of hydrochloric acid (2N, 50 ml). The mixture was extracted with dichloromethane (50 ml, ×3). The combined extracts were dried (MgSO4) and the solvent evaporated under vacuum. The oily residue was preabsorbed onto silica and purified by SPE (silica, 10 g) eluting with an ethyl acetate/cyclohexane gradient to give 3-hydroxy-4-methoxynaphtho[2,3-c]furan-1 (3H)-one (50 mg, 3.7%).