Water → HCID 86754177、化合物

反応式

[CH2:1]([O:8][NH:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:27][O:28][CH3:29])[C:24]([O-:26])=[O:25].O.[CH3:31]N(C)C=O>>[CH2:1]([O:8][N:9]=[C:10]([O:12][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:27][O:28][CH3:29])[C:24]([O:26][CH3:31])=[O:25])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

反応物 5

HCID 962Water

HCID 6228Dimethylformamide2 回

HCID 24758Sodium hydride

HCID 5129184N-phenylmethoxyacetamide

HCID 73517220HCID 73517220、化合物

生成物 1

HCID 86754177HCID 86754177、化合物収率 9.2%

実験手順

A solution of N-benzyloxyacetamide (1.65 g, 10 mmol) in 10 ml of dimethylformamide was cooled down in an ice bath, 60% sodium hydride (0.4 g, 10 mmol) was added thereto, and stirred for 10 minutes. After adding dropwise 20 ml of dimethylformamide solution of 2-bromomethylphenyl-3-methoxypropenoate (2.85 g, 10 mmol), the solution was allowed to react for 15 hours at room temperature. After completion of the reaction, the reaction solution was poured into 200 ml of water, and extracted with ethylacetate. The organic layer was rinsed with water and dried. After removing the solvent by evaporation, the residue was purified with silica gel chromatography to obtain 0.34 g of methyl 2-[2-(1-benzyloxyiminoethyl) oxymethylphenyl]-3-methoxypropenoate (yield: 9.2%). The proton NMR spectrum is 1.79 s (3H); 3.67 s (3H); 3.77 s (3H); 5.01 s (2H); 5.04 s (2H); 7.10-7.50 m (9H); 7.57 s (1H) (solvent: CDCl3).