Acetic Acid → HCID 54140188, compound

Participants

Reaction Steps

An ethereal solution of diazomethane (3.0 mL, 0.3M, 0.9 mmol) was added to 1-(3-bromo-4-methoxyphenyl)-2-nitropropene (250 mg, 0.92 mmol) dissolved in 2.5 mL of ether, and the solution was allowed to stand at room temperature for 28 h. Acetic acid (0.25 mL, 0.26 g, 4.4 mmol) was then added to the almost colorless solution, giving some gas evolution. After 15 min, the solution was diluted with 25 mL of ethyl acetate and washed with 10 mL of saturated aqueous sodium bicarbonate followed by 10 mL of saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated to give 285 mg (99% yield) of a colorless oil which crystallized upon standing. 1H NMR (400 MHz, CDCl3): δ 7.17 (d, 1H, J=2 Hz), 6.89 (dd, 1H, J=8, 2 Hz), 6.84 (d, 1H, J=8 Hz), 5.21 (dd, 1H, J=18, 8 Hz), 4.97 (dd, 1H, J=18, 6 Hz), 3.90 (s, 3H), 3.77 (dd, 1H, J=8, 6 Hz), 1.60 (s, 3H).

Provenance & Evidence