反应详情

A solution of 4-isopropylaniline (7.6 mL, 56 mmol), 2-bromoacetaldehyde diethyl acetal (5.5 mL, 36 mmol) and sodium bicarbonate (4.8 g, 57 mmol) in ethanol (60 mL) was stirred at reflux for 3 days under argon. After cooling to room temperature, the ethanol was removed in vacuo and the product was partitioned between ether and water, washed sequentially with water and brine, and dried over sodium sulfate. After removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes) yielded 4-isopropyl-N-(2,2-diethoxyethyl) aniline (8.23 g, 90%).

1. temperatureat reflux for 3 days under argon
2. customthe ethanol was removed in vacuo
3. customthe product was partitioned between ether and water
4. washwashed sequentially with water and brine
5. dry with materialdried over sodium sulfate
6. customAfter removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes)