Tetrabutylammonium Fluoride → HCID 67053009, compound

Participants

Reaction Steps

To a round bottom flask was added 2-[3-(tert-butyldimethylsilanyloxy)-4,4,4-trifluoro-1,1-dimethylbutyl]-N-[1-dimethylaminomethylidene]benzenesulfonamide (820 mg, 1.76 mmol) in 15 mL of dry THF, followed by the addition of a solution of 1M TBAF in THF (1.76 mL, 1.76 mmol). The reaction mixture was stirred at room temperature for 10 minutes, quenched with 100 mL of saturated aqueous sodium bicarbonate solution, and extracted with 250 mL of ethyl acetate. The organic layer was separated, washed with 100 mL of water and 100 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography. The column was eluted with 0-40% EtOAc/hexanes to afford 381 mg (59%) of N-[1-dimethylaminomethylidene]-2-(4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)benzenesulfonamide. MS (ES+) m/z 367 [M+H]+.

Provenance & Evidence