Hydrogen Peroxide → 4-tert-Butyl-2-methyl-pyridine 1-oxide

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Reaction Steps

Dissolve 2-methyl-4-tert-butyl-pyridine (16.60 g, 111.23 mmol) in dichloromethane (80 mL) and add methyltrioxorhenium (VII) (0.139 g, 0.56 mmol) with vigorous stirring. At ambient temperature, add 30% hydrogen peroxide (40 mL) and stir vigorously for 18 hours. Quench the reaction by adding drop wise aqueous manganese dioxide (100 mg in 20 mL). After the off-gassing ceases, the aqueous turns a cloudy gray, the layers are separated and the aqueous is re-extracted with dichloromethane (3×100 mL). The organics are pooled, desiccated, filtered and concentrated to yield the title compound analytically pure (16.60 g, 100.61 mmol). MS (ESI), m/z 166 (M+1).

Provenance & Evidence