反应详情

A solution of 2-(bromoethyl)benzene (1.73 g; 9.33 mmol) in diethylether (10 mL) was added to a stirred slurry of magnesium turnings (250 mg; 10.18 mmol) in 5 mL of ether. The reaction was initiated with a heat gun, and after the addition was complete the mixture was heated on an oil bath for 30 min. 3-Phenyl-1-propanal (1.25 g; 9.33 mmol) was added in 10 mL of ether, and reflux was continued for 1 hour. The reaction was cooled and quenched with saturated ammonium chloride, extracted into 2× ethyl acetate, and the combined organic portions were dried and concentrated. Chromatographic purification on a silica gel column (10% ethyl acetate in hexane) delivered 1.42 g(63%) of the diphenyl alcohol. 1H NMR (300 MHz, CDCl3): δ 1.84 (m, 4H); 2.61-2.76(m, 4H); 3.65 (m, 1H); 7.19-7.29 (m, 1H).

1. additionafter the addition
2. temperaturewas heated on an oil bath for 30 min
3. temperaturereflux
4. temperatureThe reaction was cooled
5. customquenched with saturated ammonium chloride
6. extractionextracted into 2× ethyl acetate
7. customthe combined organic portions were dried
8. concentrationconcentrated
9. customChromatographic purification on a silica gel column (10% ethyl acetate in hexane)