Hydrogen Peroxide → 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridine

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Reaction Steps

4-[2-(tert-Butyldimethylsiloxy)ethyl]pyridine (0.222 g, 1.00 mmol) obtained in Step 1 was dissolved in dichloromethane (2.00 mL), then methyltrioxorhenium (VII) (0.001 g, 0.005 mmol) and 30% aqueous hydrogen peroxide (1.00 mL) were added thereto, followed by stirring at room temperature for 2 hours. After completion of the reaction was confirmed by thin-layer chromatography, water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 4-[2-(tert-butyldimethylsiloxy)ethyl]pyridine-N-oxide (0.153 g, yield 64%).

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