反应详情

To a stirred solution of 4′-(2-bromoacetyl)-2′,5′-dimethylacetanilide (4.57 g) in ethanol (80 ml) was added sodium borohydride (608 mg) under ice-cooling, and the mixture was stirred for 1 hour. Acetic acid (3.7 ml) and water (200 ml) were added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in tetrahydrofuran (80 ml), and 5N aqueous sodium hydroxide solution (6.4 ml) was added to the solution under ice-cooling with stirring. The mixture was stirred for 30 minutes at room temperature, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. To the residue was added diethyl ether, and collection of the insoluble material by filtration gave 2′,5′-dimethyl-4′-oxiranylacetanilide (1.72 g).

1. temperaturecooling
2. extractionthe resulting mixture was extracted with ethyl acetate
3. washThe extract was washed with water and brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was removed in vacuo
6. dissolutionThe residue was dissolved in tetrahydrofuran (80 ml)
7. addition5N aqueous sodium hydroxide solution (6.4 ml) was added to the solution under ice-
8. temperaturecooling
9. stirringwith stirring
10. stirringThe mixture was stirred for 30 minutes at room temperature
11. additionwater was added to the reaction mixture
12. extractionthe resulting mixture was extracted with ethyl acetate
13. washThe extract was washed with water
14. dry with materialdried over anhydrous magnesium sulfate
15. customthe solvent was removed in vacuo
16. additionTo the residue was added
17. customdiethyl ether, and collection of the insoluble material
18. filtrationby filtration