反应详情

温度

0 °C

A solution (20 mL) of benzyl [2-(tert-butyldimethylsilyloxy)-4-hydroxy-1,3,3-trimethylbutyl]carbamate (1.38 g) and triethylamine (0.73 mL) in THF was added mesyl chloride (0.352 mL) at 0° C., and the mixture was stirred at 0° C. for 45 min. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To a solution (20 mL) of the residue in THF was added 1M potassium tert-butoxide—THF solution (3.8 mL). After stirring at room temperature for 1 hr, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To a solution (10 mL) of the residue in THF was added 1M tetrabutylammonium fluoride—THF solution (4 mL), and the mixture was stirred at room temperature for 17 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/2) to give the title compound as a colorless solid (yield: 842 mg, yield: 92%).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe extract was washed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. additionTo a solution (20 mL) of the residue in THF was added 1M potassium tert-butoxide—THF solution (3.8 mL)
6. stirringAfter stirring at room temperature for 1 hr
7. additionwater was added
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. concentrationconcentrated under reduced pressure
12. additionTo a solution (10 mL) of the residue in THF was added 1M tetrabutylammonium fluoride—THF solution (4 mL)
13. stirringthe mixture was stirred at room temperature for 17 hr
14. additionThe reaction mixture was added to water
15. extractionthe mixture was extracted with ethyl acetate
16. washThe extract was washed with saturated brine
17. dry with materialdried over anhydrous magnesium sulfate
18. concentrationconcentrated under reduced pressure
19. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/2)