Styrene Oxide → HCID 86602504, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4 g (10 mmol) of ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amine (example 1.1) in 12 mL of acetonitrile was treated with 2.3 mL (20 mmol) of racemic phenyloxirane and 2.12 g (20 mmol) of lithiumperchlorate. The mixture was stirred overnight at 80° C. in a sealed tube. The crude was distributed between saturated aqueous NH4Cl and Et2O and the combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 9:1 yielded 3.5 g (66%) of 2-{ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-2-phenyl-ethanol, light yellow oil, MS: 522 (MH+) and 0.475 g (9%) of 2-{ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-1-phenyl-ethanol, light yellow oil, MS: 522 (MH+).

Provenance & Evidence