Quinone → (3,4-Dimethoxyphenyl)(5-hydroxybenzofuran-3-yl)methanone

Participants

Reaction Steps

A suspension of enaminone 12 (2 g, 8.43 mmol) and compound benzoquinone Q-4 (910 mg, 8.43 mmol) in acetic acid was stirred at room temperature under an atmosphere of N2 for 5 h. The precipitate that formed was filtered, washed with water, and dried under high vacuum to afford compound 13 (1.2 g, 47%) as an off-white solid. TLC Rf=0.5 (petroleum ether-EtOAc, 7:3); 1H NMR (DMSO-d6) δ 9.43 (s, 1H), 8.59 (s, 1H), 7.57-7.43 (band, 4H), 7.12 (d, J=8.3 Hz, 1H), 6.86 (dd, J=9.0 Hz, 2.6 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H); MS (ES) m/z 299 (M+H)+.

Provenance & Evidence