Sodium borohydride → HCID 57446332, compound

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[BH4-].[Na+]>C(O)C.O>[OH:17][CH:10](/[CH:9]=[CH:8]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Procedure

To a solution of ethyl (E)-5-(2-methylphenyl)-3-oxo-4-pentenoate (37.24 g, 160.3 mmol) in ethanol (100 ml) was added sodium borohydride (3.03 g, 80.2 mmol) by small portions under ice-cooling, and the mixture was stirred as it was for 10 min. The reaction solution was diluted with water, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give a crude product of ethyl (E)-3-hydroxy-5-(2-methylphenyl)penta-4-enoate as a yellow liquid.