N-(4-hydroxyphenyl)prop-2-enamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2 (200 mg, 0.98 mmol) in 1.5 ml of MeOH in a 5 ml screw-capped vial is added 1.0 ml of 0.5 M of sodium methoxide in MeOH. The mixture is stirred at ambient temperature, and the reaction is complete in 10 min. The mixture is neutralized by addition of cation exchange resin (Dowex, 50W×8, H+) (moist pH paper). The resin is removed by filtration and washed with MeOH. The combined filtrate and wash is concentrated by rotary evaporation to yield an off-white solid (152 mg, 95%), ESI-MS (M+H)+: 164.2. 1H-NMR (acetone-d6), δ 9.15 (1H, br, NH), 7.59 (2H, d, J=9.0 Hz, NHCCH), 6.82 (2H, d, J=9.0 Hz, NHCCHCH), 6.52˜6.35 (2H, m, COCHCHH (anti to each other)), 5.70 (1H, dd, J=9.8 and 2.2 Hz, COCHCHH (syn to COCH)). The resin is removed by filtration washed with MeOH The combined filtrate and wash is concentrated by rotary evaporation