Triethylamine → 3-(Chloromethyl)-2-methoxypyridine

Participants

Reaction Steps

To a solution of (2-methoxy-pyridin-3-yl)-methanol (0.38 g, 2.74 mmol) from example 42 step A and triethylamine (0.5 mL, 3.56 mmol) in 6 mL of CH2Cl2 was added methanesulfonyl chloride (0.26 mL, 3.29 mmol) at 0° C. After 1 hr, the reaction was warmed to room temperature and stirred overnight. The reaction mixture was brought to the usual work-up to give the crude product, which was purified by chromatography (silica gel, 25% EtOAc/hexanes). 1H NMR (300 MHz, CDCl3) 8.15 (m, 1H), 7.67 (m, 1H), 6.91 (m, 1H), 4.60 (s, 2H), 4.02 (s, 3H).

Provenance & Evidence