Hydrogen Peroxide → HCID 22618299, compound

Participants

Reaction Steps

A solution of 2-benzyl-5-chloro-7-allylbenzoxazole (2.2 g, 8 mmol) in THF (12 ml) was added to a solution of di-iso-amylborane (1.13 g, 8 mmol) in THF. The reaction was allowed to stir at room temperature for 21 hours and then 3 N sodium hydroxide solution (4 ml) was added followed by 30% hydrogen peroxide (4 ml). After 3 hours, the reaction mixture was partitioned between dichloromethane and water. The dichloromethane solution was washed with water (3×100 ml) and the solvent was evaporated under reduced pressure. The residue was purified over flash chromatographic silica gel to give the title compound (600 mg) eluted with 1:1 dichloromethane/hexane. The material was recrystallized three times from toluene to give the title compound (200 mg), trip 78-80° C.

Provenance & Evidence