反应详情

A solution of 4-methyl-1,2,4-triazolidine-3,5-dione (16 g; 0.14 mmole) in dry 1:1 benzene-dimethylformamide (100 ml) was heated under reflux, with stirring under nitrogen, and potassium t-butoxide (17.62 g), was added. The resultant suspension was heated under reflux for 2 hr. and then n-pentyl vinyl ketone (12,568; 0.10 mole) in dry dimethylformamide (10 ml) added dropwise. After 2 days the mixture was allowed to cool to room temperature and partitioned between 5 M HCl (200 ml) and ethyl acetate (100 ml). The aqueous layer was extracted with ethyl acetate (5×70 ml) and the combined organic layers washed with water (2×100 ml) and brine (100 ml) and dried (Na2SO4). Evaporation in vacuo gave an oil. Recrystallisation from ethyl acetate - 60/80 petroleum ether gave 2-(3'-oxo-octyl)-4-methyl-1,2,4-triazolidine-3,5-dione (16.03 g; 66%). m.pt., 75°-76°

1. temperaturewas heated
2. temperatureunder reflux
3. temperatureunder reflux for 2 hr
4. custompartitioned between 5 M HCl (200 ml) and ethyl acetate (100 ml)
5. extractionThe aqueous layer was extracted with ethyl acetate (5×70 ml)
6. washthe combined organic layers washed with water (2×100 ml) and brine (100 ml)
7. dry with materialdried (Na2SO4)
8. customEvaporation in vacuo
9. customgave an oil
10. customRecrystallisation from ethyl acetate - 60/80 petroleum ether