Ammonium Chloride → (2-Fluoropyridin-4-yl)methanol

Participants

Reaction Steps

To a stirred solution of Benzoic acid 2-fluoro-pyridin-4-ylmethyl ester (36) (4.536 g, 19.62 mmol) in anhydrous methanol (40 ml) cooled in an ice bath, was added sodium methoxide (1.06 g, 19.62 mmol). After stirring for 30 min., excess ammonium chloride was added to the mixture. The mixture was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:1)) to afford 2.34 g (94%) of a white solid; m.p. 70-71° C.; 1H NMR (200 MHz, CDCl3) δ: 2.40 (1H, t, J=4.0 Hz), 4.78 (2H, d, J=4 Hz), 6.97 (1H, s), 7.15 (1H, m), 8.15 (1H, d, J=5.0 Hz); m/z (EI): 127 (M+).

Provenance & Evidence