Methyl iodide → 3-(benzyloxy)-1-methyl-1H-pyridin-2-one

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To a solution of 3-(benzyloxy)pyridin-2-ol (25 g, 123.00 mmol) and potassium hydroxide (10 g, 178.22 mmol, 1.45 equiv) in dimethylsulfoxide (250 mL) maintained under nitrogen atmosphere was added methyl iodide (27 g, 190.14 mmol) dropwise with stirring. The resulting solution was stirred overnight at room temperature then concentrated under vacuum. The residue was diluted with water (500 mL) then extracted with dichloromethane (2×400 mL). The combined organic layer was washed with water (3×500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give the title compound (25 g, 93%) as a light brown oil: 1H NMR (400 MHz, DMSO) delta 7.44-7.32 (m, 5H), 7.29-7.27 (m, 1H), 6.91-6.88 (m, 1H), 6.12-6.09 (m, 1H), 5.02 (s, 2H), 3.44 (s, 3H).

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