反应详情

2-(1,1-dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzamide (108 mg, 0.28 mmol) was treated with a 1M solution of TBAF in 3 mL of THF. The reaction mixture was stirred for 1 hour then diluted with 50 mL of ethyl acetate, washed with 25 mL of 1 M aqueous HCl, two 25 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude was purified by flash chromatography (12 g SiO2, hexanes to 1:1 hexanes:EtOAc) to give 2-(3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzamide as a white solid (82 mg, 93%). MS (ES+) m/z 314 [M+H]+.

1. washwashed with 25 mL of 1 M aqueous HCl, two 25 mL portions of saturated aqueous sodium bicarbonate solution
2. dry with materialdried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude was purified by flash chromatography (12 g SiO2, hexanes to 1:1 hexanes:EtOAc)