反应详情

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).

1. extractionadded water, extracted with EtOAc
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customto obtain an oil, which
6. customwas then purified by biotage
7. washeluting with 10% EtOAc/hexane