Ethyl Acrylate → Ethyl-2-(hydroxy(pyridin-3-yl)methyl)acrylate

Participants

Reaction Steps

To a solution of nicotinaldehyde (10.0 g, 93.4 mmol) in ethyl acrylate (20 mL, ˜200 mmol) at room temperature was added DABCO (0.5 g, 4.5 mmol) and the mixture was stirred overnight. Excess ethyl acrylate was removed in vacuo. The resulting crude solid was washed with hexane to give the title compound (18.5 g, 95%) as an off-white solid. δH (CDCl3) 8.62 (d, J 1.7 Hz, 1H), 8.53 (dd, J 4.8, 1.3 Hz, 1H), 7.81 (d, J 7.9 Hz, 1H), 7.28 (s, 1H), 6.42 (s, 1H), 5.93 (s, 1H), 5.63 (s, 1H), 4.18 (m, 2H), 3.20 (br s, 1H), 1.27 (t, J 7.1 Hz, 3H). LCMS (ES+) 208.2 (M+H)+.

Provenance & Evidence