反应详情

Dess-Martin reagent (770 mg) was added to a solution of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol (601 mg) in chloroform (20 mL), and the mixture was stirred at room temperature for 30 minutes. A 10% sodium thiosulfate solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. Sodium dihydrogenphosphate (1.0 g) and chlorous acid (1.6 g) were added to a solution of the resulting residue and 2-methyl-2-butene (2.3 g) in tert-butanol (15 mL)-water (5 mL), and the mixture was stirred at room temperature for one hour. The reaction solution was ice-cooled and then adjusted to a pH of less than 2 with 1 M hydrochloric acid, followed by extraction with chloroform. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1). Thereafter, the resulting solid was washed with hexane and then dried to give the title compound as a colorless powder (434 mg, 69%).

1. extractionfollowed by extraction with chloroform
2. washThe organic layer was washed with brine
3. dry with materialdried over sodium sulfate
4. filtrationAfter filtration
5. customthe solvent was evaporated under reduced pressure
6. additionSodium dihydrogenphosphate (1.0 g) and chlorous acid (1.6 g) were added to a solution of the resulting residue and 2-methyl-2-butene (2.3 g) in tert-butanol (15 mL)-water (5 mL)
7. stirringthe mixture was stirred at room temperature for one hour
8. temperaturecooled
9. extractionfollowed by extraction with chloroform
10. washThe organic layer was washed with brine
11. dry with materialdried over sodium sulfate
12. filtrationAfter filtration
13. customthe solvent was evaporated under reduced pressure
14. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)
15. washThereafter, the resulting solid was washed with hexane
16. customdried