Water → 3-(Methoxymethyl)pyridine

A solution of 3-hydroxymethylpyridine (10 g, 92 mmol) in anhydrous tetrahydrofuran (200 ml), under an atmosphere of nitrogen, was treated with sodium hydride (4 g of a 55% oil dispersion, 92 mmol) in portions. After stirring for 15 minutes iodomethane (5.7 ml, 92 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 2 hours. Water (20 ml) was added and the tetrahydrofuran evaporated. The residue was partitioned between water (50 ml) and dichloromethane (70 ml). The organic layer was separated, dried (sodium sulphate) then evaporated. The crude product was purified by column chromatography on silica using ethyl acetate. The title compound was obtained (11 g, 93%) as an oil, δH (250 MHz, CDCl3) 3.42 (3H, s), 4.48 (2H, s), 7.27-7.32 (1H, m), 7.66-7.71 (1H, m), 8.53-8.60 (2H, m).