Styrene Oxide → 2-[2-Methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 114 mg (0.275 mmol) of 2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole (example 51.2) in 1 mL of acetonitrile were added 0.063 mL (0.55 mmol) of racemic phenyloxirane and 58 mg (55 mmol) of lithiumperchlorate. After stirring at 80° C. for 18 hrs, the mixture was distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 77 mg (52%) of 2-[2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanol, MS: 534 (MH+).

Provenance & Evidence