Chloroform → 3-Chloromethyl-2-methyl-pyridine 1-oxide

Participants

Reaction Steps

Prepared essentially according to the procedure of I. M. Bell et al., J. Med. Chem. 41, 2146–2163 (1998). To a stirred solution of the crude 3-hydroxymethyl-2-methyl-pyridine of Step B (1.35 g, 9.53 mmol) in chloroform (50 mL) was added 90% m-chloroperbenzoic acid (2.0 g, 10.4 mmol). After stirring overnight at room temperature, an additional quantity of 90% m-chloroperbenzoic acid (1.0 g, 5.2 mmol) was added. The reaction mixture was stirred for an additional 3 hours and then quenched with saturated aqueous sodium bicarbonate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow solid. Purification by flash chromatography using a solvent system of 3% methanol in chloroform provided 0.85 g of the title compound as a brown-orange amorphous solid.

Provenance & Evidence