反应详情

3′-(N-cyclopropylaminomethyl)acetophenone (0.35 g; 1.85 mmol) and potassium carbonate (0.36 g; 2.64 mmol) were added to N,N-dimethylformamide (15 ml). While the mixture was stirred in an ice bath, 1-bromo-6,6-dimethyl-2-hepten-4-yn (0.35 g; 1.76 mmol) in N,N-dimethylformamide (5 ml) was added dropwise. After completion of the addition, the mixture was removed from the ice bath, and stirred for 18 hours at room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.33 g of the target compound (yield: 60.6%).

1. additionAfter completion of the addition
2. customthe mixture was removed from the ice bath
3. stirringstirred for 18 hours at room temperature
4. additionThe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
5. extractionfollowed by extraction with ethyl acetate (100 ml)
6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)