Triacetoxyperiodinane → HCID 67053017, compound

Participants

Reaction Steps

To a round bottom flask was added N-[1-dimethylaminomethylidene]-2-(4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)benzenesulfonamide (367 mg, 1.00 mmol) in 25 mL of dry dichloromethane, followed by the addition of Dess-Martin periodinane (600 mg, 1.42 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate solution and extracted with 250 mL of ethyl acetate. The organic layer was separated, washed with 50 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Dichloromethane was added to the residue and the solid which did not dissolve in dichloromethane was filtered. The mother liquor was then concentrated in vacuo and the crude mixture was purified by flash chromatography. The column was eluted with 0-40% EtOAc/hexanes to afford 345 mg (95%) of N-[1-dimethylaminomethylidene]-2-(4,4,4-trifluoro-1,1-dimethyl-3-oxobutyl)benzenesulfonamide. MS (ES+) m/z 365 [M+H]+.

Provenance & Evidence