Hydrogen Peroxide → HCID 67490784, compound

Participants

Reaction Steps

A solution of a borane-tetrahydrofuran complex in tetrahydrofuran (1 M, 187 mL, 187 mmol) was added dropwise to a solution of 2-(tritylamino)methyl-5,6-dihydro-4H-pyran (22.2 g, 62.4 mmol) in tetrahydrofuran (180 mL) at room temperature over 20 minutes. After stirring at room temperature for 2.5 hours, the reaction solution was ice-cooled, and a 3N sodium hydroxide solution (208 mL, 624 mmol) was added dropwise over 10 minutes. Subsequently a 31% hydrogen peroxide solution (69 mL, 629 mmol) was added dropwise at the same temperature over 10 minutes, and then the mixture was stirred at room temperature for one hour. The reaction solution was extracted with diethyl ether (2×300 mL). The combined organic layers were washed with water (300 mL) and brine (300 mL), and then dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and then the residue was suspended in a mixed solvent of dichloromethane/hexane (1:1, 80 mL). The insoluble material was removed by filtration, and then the filtrate was evaporated under reduced pressure to give 18.54 g (80%) of the title compound as a pale yellow gummy solid.

Provenance & Evidence