Acetone → HCID 89188746, compound

Participants

Reaction Steps

The compound was prepared according to general procedure E with syringaldehyde (2.1 mmol) in dry acetone (10 ml), anhydrous K2CO3 (2.7 mmol), and ethylbromoacetate (2.5 mmol) at reflux for 4 h. Ethanol was added and evaporated by azeotropic distillation with Ethylbromoacetate. The crude product was purified by silica gel chromatography (eluent dichloromethane). 221 mg of purified compound were obtained (31% yield). 1H NMR (250 MHz, CDCl3): δ 1.30 (t, J=7.2 Hz, 3H), 4.24 (q, J=7.4 Hz, 2H), 4.81 (s, 2H), 4.84 (s, 2H), 6.98 (d, J=8.7 Hz, 1H), 8.0 (dd, J=8.9 and 1.9 Hz, 1H), 8.44 (d, J=1.9 Hz, 1H), 9.91 (s, 1H) 13C NMR (126 MHz, CDCl3): δ 15.3, 62.7, 67.2, 115.0, 121.3, 131.2, 135.9, 135.9 (2C), 163.3, 165.0, 168.9, 191.2

Provenance & Evidence