HCID 89601195, compound → HCID 89601788, compound

Participants

Reaction Steps

To a stirred solution of (5E)-2-(4-bromo-2,6-dichloro-phenyl)-3-methoxy-5-(2-pyridylmethylene)cyclopent-2-en-1-one (235 mg, 0.55 mmol) in glacial AcOH (2.4 ml) at 0°C. was added zinc dust (126 mg, 1.94 mmol) portionwise over 10 minutes. The reaction was stirred at room temperature for 2 hours and then diluted with EtOAc (25 ml), filtered through Celite and washed through with further EtOAc (2×20 ml). The filtrate was evaporated to dryness under reduced pressure and then azeotroped with toluene and then MeOH to give the desired product (235 mg, 99%) as a brown gum. 1H NMR (400 MHz, CDCl3) δ ppm 8.52 (d, 1H), 7.60 (dd, 1H), 7.45 (2×s, 2×1H), 7.25 (d, 1H), 7.15 (dd, 1H), 3.80 (s, 3H), 3.45-3.35 (1H, m), 3.20-3.10 (m, 1H), 3.00-2.90 (1H, m), 2.90-2.85 (m, 2H).

Provenance & Evidence