Triethylamine → HCID 86669877, compound

Participants

Reaction Steps

To a solution of 3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-ol (Example 9, 115 mg, 0.377 mmol), dimethylaminopyridine (4.60 mg, 0.038 mmol), and triethylamine (0.262 mL, 1.883 mmol) in anhydrous dichloromethane (2 mL) was added perfluoro-1-butanesulfonyl fluoride (0.102 mL, 0.565 mmol) dropwise at room temperature under nitrogen. The mixture was stirred at room temperature for 4.5 hr and allowed to stand in the freezer overnight and quenched by the addition of saturated aqueous sodium bicarbonate solution (3 mL). The dichloromethane layer was separated and the aqueous layer was re-extracted with dichloromethane (2 mL). The combined organic solutions were dried over sodium sulfate, filtered through a silica gel pad and concentrated under reduced pressure to give 3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (160 mg, 0.272 mmol, 72.3% yield) as a white solid. LC/MS M+1=588

Provenance & Evidence