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

Temperature

-78 °C

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.

1. customthe resulting brown solution was quenched with a mixture of Et2O/saturated Na2SO3 solution
2. stirringThe mixture was stirred at ambient temperature for 1 h
3. customto give a colorless solution
4. customThe organic layer was separated
5. washwashed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-9cf0a8f8506b4b01b5e8a8897360f1cc

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067921B2