Chloromethyl Methyl Ether → HCID 11701122, compound

Participants

Reaction Steps

Under argon atmosphere, into a solution of 5-chloro-3-pyridinol (5.0 g, 38.6 mmol) in 100 mL of dry tetrahydrofuran at room temperature was added 60% sodium hydride (1.85 g, 46.3 mmol). After stirring the mixture for 1 hour at room temperature, a solution of chloromethyl methyl ether (3.42 g, 42.6 mmol) in 10 mL of dry tetrahydrofuran was added over 10 min. The resulting mixture was heated to reflux for 16 hours. The solvent was evaporated, and the residue was diluted with ethyl acetate, then washed with 1N aq. NaOH. The combined organic layer was then concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v/), gave the desired product (6.52 g, 97%).

Provenance & Evidence