Hydrogen Peroxide → cis-7-Methyl-1,4-dioxa-spiro[4.5]decan-8-ol

Participants

Reaction Conditions

Reaction Steps

To a tetrahydrofuran (100 mL) solution of 7-methyl-1,4-dioxa-spiro[4.5]-decan-8-one (Tetrahedron Asymmetry 2001, 12, 1683) (9.50 g), K-Selectride (1.0 mol/L tetrahydrofuran solution, 65 mL) was gradually added at −78° C. After 1 hour, the reaction mixture was warmed to 0° C., and a 1 N aqueous sodium hydroxide solution (120 mL) and 30% aqueous hydrogen peroxide (100 mL) were gradually added thereto. The purified aqueous mixture was stirred overnight, followed by two extractions with dichloromethane. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated. The residue was purified by chromatography (hexane/ethyl acetate=4:1→2:1→1:1) to obtain the title compound (8.18 g, 85%) as a colorless oil.

Provenance & Evidence