Dimethyl Carbonate → HCID 68603292, compound

Participants

Reaction Steps

A mixture of 3-phenylcycloheptanone (1.88 g, 9.99 mmol) and 5 drops of methanol in dimethyl carbonate (1.68 mL, 20.0 mmol) was treated with sodium hydride (60% dispersion, 800 mg, 20.0 mmol). The reaction was then refluxed for 2 hours before being cooled back to room temperature. The reaction was quenched with 2 M hydrochloric acid and extracted with ether, then chromatographed on silica gel (15% ethyl acetate/hexane, eluant) to afford the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.26 (m, 5H), 3.81 (dd, J=11.70, 3.77 Hz, 1H), 3.63 (s, 3H), 3.17 (m, 2H), 1.86 (m, 6H); MS (DCI+) m/z 247 (M+H)+, 264 (M+NH4)+.

Provenance & Evidence