Trifluoromethanesulfonic anhydride → HCID 86669914, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoromethanesulfonic anhydride (0.012 mL, 0.069 mmol) was added to a solution of 5,5-difluoro-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-ol (Preparation 66D, 0.020 g, 0.046 mmol) in pyridine (5.0 mL) at 0° C. over a period of 5 min. The reaction mixture was stirred at 0° C. for ten minutes, warmed to room temperature, and stirred overnight. The reaction mixture was concentrated, and the yellowish-brown residue was partitioned between ethyl acetate (10 mL) and water (10 mL). The ethyl acetate layer was collected, washed with 1N aqueous Hydrochloric acid (10 mL), saturated aqueous solution of sodium bicarbonate (10 mL), brine (10 mL), and dried over sodium sulfate. Concentration followed by purification by silica gel chromatography eluting with a mixture of ethyl acetate and hexane (10%-20%) afforded 5,5-difluoro-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl trifluoromethanesulfonate (0.024 g, 0.042 mmol, 92% yield) as a viscous liquid. The product had an HPLC ret. time=3.34 min. (condition B). LC/MS M+1=566.3, 568.4.

Provenance & Evidence