反应详情

温度

90 °C

Trifluoroacetamidine (2.47 g) and diethyl ethylidenemalonate (3.64 ml) were dissolved in ethanol (50 ml) and the mixture was stirred at 90° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water. The mixture was adjusted to pH 4 with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and the obtained oil (570 mg) was dissolved in carbon tetrachloride (45 ml). N-Bromosuccinimide (381 mg), 2,2′-azobis(2-methylpropionitrile) (16 mg) and potassium carbonate (2.90 g) were added and the mixture was heated under reflux for 30 min. The reaction mixture was cooled to room temperature, and water was added. The aqueous layer was separated, adjusted to pH 3 with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the object compound (313 mg) as a powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in water
3. extractionextracted with ethyl acetate
4. washThe extract was washed with water and saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography
8. dissolutionthe obtained oil (570 mg) was dissolved in carbon tetrachloride (45 ml)
9. additionN-Bromosuccinimide (381 mg), 2,2′-azobis(2-methylpropionitrile) (16 mg) and potassium carbonate (2.90 g) were added
10. temperaturethe mixture was heated
11. temperatureunder reflux for 30 min
12. temperatureThe reaction mixture was cooled to room temperature
13. additionwater was added
14. customThe aqueous layer was separated
15. extractionextracted with ethyl acetate
16. washThe extract was washed with saturated brine
17. dry with materialdried over anhydrous sodium sulfate
18. concentrationconcentrated under reduced pressure
19. customThe obtained residue was purified by silica gel column chromatography