反应详情

温度

111 °C

The mixture of 3-oxo-1-phenylcyclohexanecarbonitrile (2.62 g), ethylene glycol (3.65 mL) and pyridinium p-toluene sulfonate (1 spatula) in benzene (40 mL) was stirred at 111° C. with Dean-Stark apparatus overnight. After cooling down to room temperature, the mixture was washed with saturated sodium bicarbonate and the organic layer was separated. The aqueous layer was extracted with dichloromethane 3 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified by Flash Chromatography with from 25% ethyl acetate/75% hexane to 30% ethyl acetate/70% hexane over 20 minutes. The title compound was obtained as a white solid (1.66 g, 48% yield in 2 steps). 1H NMR (400 MHz, CDCl3) δ 1.56 (1H, dt, J=4, 16 Hz), 1.70-1.79 (1H, m), 1.89-1.96 (3H, m), 2.06-2.28 (3H, m), 3.89-3.97 (2H, m), 4.03-4.12 (2H, m), 7.28-7.32 (1H, m), 7.36-7.39 (2H, m), 7.48-7.51 (2H, m). HPLC purity (retention time): 95% (1.62 min, method C). MS: 266.37 (M+Na+).

1. temperatureAfter cooling down to room temperature
2. washthe mixture was washed with saturated sodium bicarbonate
3. customthe organic layer was separated
4. extractionThe aqueous layer was extracted with dichloromethane 3 times
5. dry with materialthe combined organic layers were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude material was purified by Flash Chromatography with from 25% ethyl acetate/75% hexane to 30% ethyl acetate/70% hexane over 20 minutes