反应详情

To a solution of 5,6,7,8-tetrahydro-cyclohepta[b]thiophen-4-one (0.84 g, 5 mmol), prepared by the method of M. P. Cagniant (Bull. Soc. Chim. France, 1956, 1152-1163), in dimethylcarbonate (6 mL) was added a 60% dispersion of sodium hydride in oil (0.4 g, 10 mmol) and a few drops of dry methanol. The reaction mixture was heated at reflux for 4 hours, then cooled, quenched with 2 N hydrochloric acid solution, and the desired product was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, concentrated and chromatographed on silica gel, eluting with 20% ethyl acetate:hexane to provide the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.34 (d, J=5.42 Hz, 1H,), 7.28 (d, J=5.42 Hz, 1H), 4.04 (dd, J=10.8, 3.39 Hz, 1H), 3.66 (s, 3H), 3.80 (m, 4H), 3.14 (m, 2H); MS (DCI/NH3) m/z 225 (M+H)+, 242 (M+NH4)+.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 4 hours
3. temperaturecooled
4. customquenched with 2 N hydrochloric acid solution
5. extractionthe desired product was extracted with ethyl acetate
6. dry with materialThe combined organic layers were dried over magnesium sulfate
7. concentrationconcentrated
8. customchromatographed on silica gel
9. washeluting with 20% ethyl acetate