Hydrogen Peroxide → HCID 9944208, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2-chlorobenzyl)-5-chloro-7-allylbenzoxazole (5.0 g, 0.018 mole) in THF was added to a solution of di-iso-amylborane prepared from borane-THF complex (1.60g, 0.018 mol) and 2-methyl-2-butene (2.80 g, 0.04 mol) in THF. The reaction mixture was stirred overnight and cooled to −20° C. then treated with 3 N sodium hydroxide (6.5 ml) and 30% hydrogen peroxide (6.5 ml). The reaction mixture was allowed to warm to room temperature and stirred for 4 hours. The product was isolated by partitioning between dichloromethane and water. Flash chromatography over flash chromatographic silica gel with dichloromethane afforded nearly pure title compound which was recrystallized from ether-hexane to give 290 mg of pure title compound, mp 66-68° C.

Provenance & Evidence