Dimethyl Carbonate → HCID 68528872, compound

Participants

Reaction Steps

5,6,7,8-Tetrahydro-cyclohepta[b]furan-4-one (J. Chem. Soc., Perkin Trans. 1, 1980, 2081-2083) (0.1 g, 0.7 mmol) in dimethylcarbonate (2 mL) was treated with a 60% dispersion of sodium hydride (0.06 g, 0.15 mmol) as described in Example 1A to yield the title product. NMR in CDCl3 indicates a 70:30 mixture of keto and enol forms: 1H NMR (300 MHz, CDCl3) δ 13.02 (s, 0.3H), 7.29 (d, J=2.03 Hz, 0.4H), 7.23 (d, J=2.03 Hz, 0.6H), 6.73 (d, J=2.03 Hz, 0.6H), 6.72 (d, J=2.03 Hz, 0.4H) 3.78 (s, 1.2H), 3.75 (s, 1.8H), 3.72 (dd, J=9.99, 3.9 Hz, 0.6H), 3.02 (m, 1.2H), 2.96 (t, J=6.6 Hz, 0.8H), 2.56 (t, 0.8H), 1.84-2.2 (m, 3.5H); MS (DCI/NH3) m/z 209 (M+H)+.

Provenance & Evidence