反应详情

温度

0 °C

Into a reactor was introduced 102 mL (82.0 mmol; 0.80 M THF solution) of ethylmagnesium bromide under a nitrogen atmosphere. The contents were cooled to 0° C. Thereto was gradually added dropwise a solution prepared by mixing 20.0 g (74.5 mmol) of 4,4′-bis(dimethylamino)benzophenone and 40 mL of THF. This mixture was stirred at room temperature for 5 hours. Saturated aqueous ammonium chloride solution was added to the resultant reaction mixture, and the metal salt yielded was removed by Celite filtration. The organic layer was separated from the filtrate and then extracted with toluene. Thereafter, the solvent was removed under reduced pressure. The concentrate was dissolved in 150 mL of toluene, and 0.1 g of p-toluenesulfonic acid monohydrate was added thereto. Azeotropic dehydration was conducted with toluene refluxing. After being cooled, the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, subsequently dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. This concentrate was purified by column chromatography to obtain 13.6 g (65%) of light-yellow crystals. 1H-NMR (CDCl3) δ 1.77 (d, J=7.0 Hz, 3H), 2.92 (s, 6H), 2.98 (s, 6H), 5.94 (q, J=7.0 Hz, 1H), 6.58-6.79 (m, 4H), 7.02-7.18 (m, 4H).

1. additionThereto was gradually added dropwise a solution
2. customprepared
3. customreaction mixture
4. customthe metal salt yielded
5. customwas removed by Celite filtration
6. customThe organic layer was separated from the filtrate
7. extractionextracted with toluene
8. customThereafter, the solvent was removed under reduced pressure
9. dissolutionThe concentrate was dissolved in 150 mL of toluene
10. addition0.1 g of p-toluenesulfonic acid monohydrate was added
11. temperatureAfter being cooled
12. washthe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
13. dry with materialsubsequently dried with anhydrous magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThis concentrate was purified by column chromatography