Water → 5-(Benzyloxy)pentan-2-ol

Reaction equation

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

Participants

Procedure

Sodium borohydride (236 mg) was added to a mixed solution of 5-benzyloxy-2-pentanone (1.09 g, 5.67 mmol) in methanol (50 mL) in an ice bath, followed by stirring. After completion of the reaction, water was added to the reaction solution in an ice bath, and methanol was evaporated. The pH was adjusted to 4 with 2 mol/L hydrochloric acid. After extraction with chloroform-water, the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 957 mg of the title compound (yield: 87%) as a colorless solid.