反应详情

Potassium t-butoxide (2.59 g, 23.1 mmol) was dissolved in DMF (100 ml), and thereto was added 4-phenyl-1H-imidazole (3.00 g, 21 mmol) with stirring. The mixture was stirred at room temperature for 30 minutes, and thereto was added allyl bromide (3.50 g, 31.5 mmol). The mixture was stirred at 40° C. for 4 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was dissolved in pyridine (24 ml), and thereto were added successively triethylamine (17.9 g, 17.7 mmol) and 4-toluoyl chloride (3.7 g, 16.3 mmol), and the mixture was stirred at 60° C. for 5 hours. To the reaction solution was added water (50 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 1N diluted hydrochloric acid, and saturated saline, and dried over magnesium sulfate. Then, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (760 mg, 30%).

1. stirringThe mixture was stirred at room temperature for 30 minutes
2. stirringThe mixture was stirred at 40° C. for 4 hours
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with water and saturated saline
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was removed under reduced pressure
7. dissolutionThe resulting residue was dissolved in pyridine (24 ml)
8. stirringthe mixture was stirred at 60° C. for 5 hours
9. extractionthe mixture was extracted with ethyl acetate
10. washThe organic layer was washed with water, 1N diluted hydrochloric acid, and saturated saline
11. dry with materialdried over magnesium sulfate
12. customThen, the solvent was evaporated under reduced pressure
13. customthe resulting residue was purified by silica gel column chromatography