Ethyl benzoylformate → (-)-Ethyl mandelate

反応式

[BH4-].[Na+].C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[C:13]1([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[OH:25][C@H:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

参加物

反応条件

温度: 70 °C

実験手順

To a dispersion of 0.43 g (11.3 mmol) of sodium borohydride in THF (35 ml), there was added 1.70 g (11.3 mmol) of L-(+)-tartaric acid, and the mixture was heated under reflux for four hours in an oil bath at 70° C. with stirring. The resulting mixture was cooled in a cryostat at -20° C., a solution of 0.5 g (2.8 mmol) of ethyl phenylglyoxylate in THF (5 ml) was added dropwise over a period of ten minutes, and stirring was continued for 19 hours. The reaction mixture was treated in the same manner as in Example 6, giving 0.44 of ethyl (R)-(-)-2-hydroxy-2-phenylacetate, having a specific rotation [α]D16 of -109° (cl. 00, CHCl3).