Diethyl Ether → Octahydro-2H-inden-2-one

Participants

Reaction Conditions

Reaction Steps

To 33.6 g (155 mmol) of finely ground pyridinium chlorochromate, stirred in 300 mL of dry dichloromethane, was added 7.0 g (50 mmol) of (2 alpha and 2 beta)-octahydro-1H-inden-2-ol in 30 mL of dichloromethane. After stirring for 2 h at 20° C., 300 mL of ether was added, the organic solution decanted from the gummy precipitate and the latter extracted with 5×100 mL of ether. The combined organic solutions were filtered through 450 g of silica gel and the latter washed with ether. Concentration of the filtrates and distillation gave 5.5 g (80%) of (3a alpha, 7a alpha)octahydro-2H-inden-2-one bp 110°-112° C. (18 mm); TLC Rf of 0.29 (SiO2, dichloromethane, molybdophosphoric acid-colorless on blue-green).

Provenance & Evidence