Acetic Acid → Ethyl 3-[3-(benzyloxy)phenyl]-3-oxopropanoate

反応式

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(O)(=O)C.[C:24](=O)([O:28]CC)[O:25][CH2:26][CH3:27]>>[CH2:26]([O:25][C:24](=[O:28])[CH2:16][C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)=[O:17])[CH3:27]

参加物

反応物 4

HCID 176Acetic Acid

HCID 7766Diethyl Carbonate

HCID 24758Sodium hydride

HCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-one

生成物 1

HCID 10334847Ethyl 3-[3-(benzyloxy)phenyl]-3-oxopropanoate収率 84%

反応条件

温度: 60 °C

実験手順

1-(3-Benzyloxyphenyl)ethanone (218 g, 966.10 mmol) was dissolved in diethyl carbonate and sodium hydride (60% oil) (46.37 g, 1.15 mmol) was slowly added thereto at 0° C., and then stirred for 3 hours at 60° C. After the reaction was completed, ice water and acetic acid were added to the reaction mixture, extracted with ethyl acetate/saturated sodium chloride, the organic layer was separated, and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:10) to obtain 3-(3-benzyloxyphenyl)-3-oxopropionate ethyl ester (184.68 g, yield 84%) in an oil state.