反应详情

温度

0 °C

In dichloromethane (25.0 ml), 5-ethyl-2-methyl-pyridine (2.31 g) was dissolved. The reaction solution was cooled to 0° C. and added with meta-chloroperbenzoic acid (4.43 g), followed by stirring at room temperature for 2.5 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. Subsequently, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resulting residue in dichloromethane (40.0 ml). The reaction solution was added with trifluoroacetic anhydride (5.6 ml) and subjected to thermal reflux for 3.5 hours. After the reaction solution had been cooled to room temperature, the solvent was distilled off. The residue obtained was dissolved in methanol (80.0 ml). After having been cooled to 0° C., the reaction solution was added with a 12.5% sodium methoxide/methanol solution and adjusted to pH 10, followed by stirring at room temperature for 16.5 hours. After the solvent had been distilled off, the residue was added with distilled water and extracted with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resulting residue in chloroform (50.0 ml). The reaction solution was added with manganese dioxide (chemically processed product) (7.44 g) and then stirred at room temperature for 18 hours. The reaction solution was filtrated through Celite. The solvent in the filtrate was distilled off and the residue obtained was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (515.6 mg) as a yellow oily substance.

1. extractionsubjected to extraction with chloroform
2. washSubsequently, the organic layer was washed with saturated saline solution
3. dry with materialdried with anhydrous sodium sulfate
4. filtrationThe drying agent was filtrated out
5. distillationthe solvent was then distilled off
6. dissolutionby dissolving the resulting residue in dichloromethane (40.0 ml)
7. additionThe reaction solution was added with trifluoroacetic anhydride (5.6 ml)
8. temperaturethermal reflux for 3.5 hours
9. temperatureAfter the reaction solution had been cooled to room temperature
10. distillationthe solvent was distilled off
11. customThe residue obtained
12. temperatureAfter having been cooled to 0° C.
13. stirringby stirring at room temperature for 16.5 hours
14. distillationAfter the solvent had been distilled off
15. additionthe residue was added with distilled water
16. extractionextracted with chloroform
17. washThe organic layer was washed with saturated saline solution
18. dry with materialdried with anhydrous sodium sulfate
19. filtrationThe drying agent was filtrated out
20. distillationthe solvent was then distilled off
21. dissolutionby dissolving the resulting residue in chloroform (50.0 ml)
22. additionThe reaction solution was added with manganese dioxide (chemically processed product) (7.44 g)
23. stirringstirred at room temperature for 18 hours
24. filtrationThe reaction solution was filtrated through Celite
25. distillationThe solvent in the filtrate was distilled off
26. customthe residue obtained
27. customwas then purified through silica gel column chromatography (chloroform/ethyl acetate)