Potassium bisulfate → HCID 11598744, compound

Participants

Reaction Steps

76 mg (0.12 mmol) of rac 4-(1-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzoic acid methyl ester in 4 ml of a mixture of acetonitrile:water (9:1) were treated with 250 mg (0.46 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 for 3 h. 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 and dried (Na2SO4) and evaporated. Column chromatography on ISOLUTE Flash NH2 with a gradient of EtOAc/n-heptane to EtOAc gave 30 mg (48%) of rac 4-{1-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzoic acid methyl ester as a colorless oil, MS: 513 (M−H)−.

Provenance & Evidence