m-Chloroperbenzoic acid → 3-Chloromethyl-2-methyl-pyridine 1-oxide

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Reaction Steps

To a stirred solution of 3-chloromethyl-2-methylpyridine (0.50 g, 3.5 mmol) from step 2 above in CHCl3 (40 mL) was added MCPBA (1.1 g of 50% MCPBA by weight; 3.5 mmol). After 1.5 h, the solution was extracted with saturated aqueous NaHCO3 (40 mL), water (40 mL), dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine-N-oxide was obtained as a solid (TLC: Rf = 0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)).

Provenance & Evidence