Sodium borohydride → Methyl 5-(3-(3-hydroxybutyl)phenyl)isoxazole-3-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[CH:11]=2)[O:7][N:6]=1)=[O:4].[BH4-].[Na+]>CO>[OH:20][CH:18]([CH3:19])[CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([C:8]2[O:7][N:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=2)[CH:15]=[CH:14][CH:13]=1Participants
4
Procedure
To a mixture of 5-(3-(3-Oxo-butyl)-phenyl)-isoxazole-3-carboxylic acid methyl ester (860 mg, 3.15 mmol) in methanol (15 mL)at room temperature was added NaBH4 (178 mg, 4.7 mmol) with stirring. After 30 min, the reaction mixture was partitioned between ethyl acetate and 3N HCl. The organic layer was washed with brine, dried over Na2SO4, filtered, evaporated in vacuo to provide the titled compound as a light brown oil (850 mg, 99% yield).