Benzaldehyde → Ethyl 3-hydroxy-2-methyl-3-phenylpropanoate
反応式
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:10][CH3:11]>>[C:2]1([CH:1]([OH:8])[CH:10]([CH3:11])[C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1参加物
3
反応条件
- 温度
- -78 °C
実験手順
50 mmol (5.10 ml) of benzaldehyde are added at -78° C. to the manganous enolate of ethyl propionate, prepared as indicated above. After stirring for 10 seconds at -78° C., the reaction medium is hydrolyzed by the dropwise addition of a saturated solution of (NH4)2SO4. After decantation, filtration on hyflo-supercel and evaporation of the solvents under vacuum, ethyl 3-phenyl-3-hydroxy-2-methylpropionate is isolated by low pressure liquid chromatography on 15 μm silica gel using cyclohexane/ethyle acetate (90/10) as the eluent. Yield=72%. Erythro/threo=61/39.
後処理
- customprepared
- filtration