反应详情

To a solution of 80% technical grade 2-cycloheptenone (3.48 mL, 25 mmol) and triethylamine (1 mL) in toluene were added phenylisocyanate (5.95 g, 50 mmol) and nitroethane (2.24 g, 30 mmol) in four portions over 1 hour. The reaction mixture was stirred at ambient temperature for 4 hours, the precipitate was filtered off and the filtrate was concentrated. The obtained residue was chromatographed, eluting with 20% ethyl acetate/hexane to yield the title compound: 1H NMR (300 MHz, CDCl3) δ 4.81 (m, 1 H), 4.06 (d, J=11.87 Hz, 1 H), 2.47 (m, 2 H), 2.02 (m, 3 H), 1.93 (m, 2 H), 1.81 (m, 2 H), 1.67 (m, 2 H); MS (DCI/NH3) m/z 168 (M+H)+.

1. filtrationthe precipitate was filtered off
2. concentrationthe filtrate was concentrated
3. customThe obtained residue was chromatographed
4. washeluting with 20% ethyl acetate/hexane