tert-Butyl hydroperoxide → 4-(trifluoromethyl)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(trifluoromethyl)-1H-indene (1.1 g, 6 mmol) in anhydrous dichloromethane (80 mL) at −78° C. was added a 5.5 M solution of tert-butyl hydroperoxide in n-decane (1.3 mL) followed by titanium tetrachloride (0.79 mL, 7.2 mmol). After being stirred at −78° C. for 1 h, the resulting brown solution was quenched with a mixture of Et2O/saturated Na2SO3 solution. The mixture was stirred at ambient temperature for 1 h to give a colorless solution. The organic layer was separated and washed with brine, dried over MgSO4 and concentrated to give the crude product (1.2 g) as a solid. LC/MS calculated for C10H2F3O: (M+H)+201; found 201.0.

Provenance & Evidence