反应详情

A mixture of N-{3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl}acetamide 2 (12.7 g, 0.055 mol) and sodium hydride (60% in oil) (2.5 g) in DMF (150 ml) under nitrogen was stirred at room temperature for 30 minutes. The solution was then cooled to 0° C., and a solution of ethyl iodide (9.38 g, 0.063 mol) in DMF (50 ml) was added slowly dropwise. The mixture was then stirred at room temperature for one hour. The DMF was removed under high vacuum, water (200 ml) was added to the residue and the mixture was extracted with ethyl acetate (2×200 ml). The combined ethyl acetate extracts were washed with water (150 ml) and brine (100 ml), dried over sodium sulfate, filtered and concentrated to dryness to give the crude product. Compound 5 was obtained after recrystallization from hexane (7.9 g). M. P. (Hexane): 109-112° C.

1. temperatureThe solution was then cooled to 0° C.
2. stirringThe mixture was then stirred at room temperature for one hour
3. customThe DMF was removed under high vacuum, water (200 ml)
4. additionwas added to the residue
5. extractionthe mixture was extracted with ethyl acetate (2×200 ml)
6. washThe combined ethyl acetate extracts were washed with water (150 ml) and brine (100 ml)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to dryness
10. customto give the crude product