Potassium bisulfate → Rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde

Participants

Reaction Steps

90 mg (0.15 mmol) of rac 1-(1-phenyl-2-p-tolyloxy-ethoxy)-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-benzene in 3 ml of a mixture of acetonitrile:water (9:1) were treated with 100 mg (0.18 mmol) of ceric ammonium nitrate at room temperature overnight. An additional 100 mg (0.18 mmol) of ceric ammonium nitrate were added and stirring was continued. EtOAc and 1M KHSO4 were added and the phases were separated. The inorganic one was extracted with EtOAC, the combined organic phases were washed with brine, dried (Na2SO4) and evaporated. Column chromatography on silica gel gave 44 mg (48%) of rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde, MS: 663 (M+OAc)−.

Provenance & Evidence