Methanol → 5-Benzyloxypent-2-yl acetate

Reaction equation

[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][CH2:16][CH2:17][CH2:18]C(O)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO>N1C=CC=CC=1>[C:5]([O:4][CH:1]([CH2:18][CH2:17][CH2:16][O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2])(=[O:7])[CH3:6]

Participants

Procedure

Acetic anhydride (1.86 mL) was added to a mixed solution of 5-benzyloxypentan-2-ol (957 mg, 4.93 mmol) in pyridine (1.8 mL) in an ice bath. After completion of the reaction, methanol (1.6 mL) was added to the reaction solution in an ice bath, and the solvent 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 420 mg of the title compound (yield: 36%) as a colorless oil.