Sodium borohydride → (3-(But-3-en-1-yl)phenyl)methanol

Participants

Reaction Steps

A mixture of 3-(but-3-en-1-yl)benzaldehyde (300 mg, 1.873 mmol) in MeOH (5 mL) was added sodium borohydride (142 mg, 3.75 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (3-(but-3-en-1-yl)phenyl)methanol (167 mg, 1.029 mmol, 55.0% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.45-7.10 (m, 4H), 5.88 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.15-4.94 (m, 2H), 4.70 (br. s., 2H), 2.84-2.71 (m, 2H), 2.48-2.34 (m, 2H).

Provenance & Evidence