反应详情

tert-Butyldimethylchlorosilane (8.7 g) and imidazole (3.9 g) were added to a solution of 3-(4-bromophenoxy)propan-1-ol in N,N-dimethylformamide (193 mL) under ice-cooling, and the mixture was stirred at room temperature for 40 minutes. The reaction solution was ice-cooled and water and a saturated ammonium chloride solution were added, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1). Pyrrolidine (4.82 mL) and triethylamine (8.86 mL) were added to a solution of the resulting crude product in tetrahydrofuran (145 mL) under ice-cooling, and the mixture was stirred at room temperature for 27 hours. The reaction solution was ice-cooled and a saturated ammonium chloride solution was added, followed by extraction with a mixture of hexane-chloroform (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→80:1) to give the title compound (7.88 g, 79% (two steps)).

1. temperaturecooling
2. temperaturecooled
3. extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
4. dry with materialThe organic layer was dried over sodium sulfate
5. filtrationfiltered
6. customThe solvent was then evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1)
8. additionPyrrolidine (4.82 mL) and triethylamine (8.86 mL) were added to a solution of the resulting crude product in tetrahydrofuran (145 mL) under ice-
9. temperaturecooling
10. stirringthe mixture was stirred at room temperature for 27 hours
11. temperaturecooled
12. additiona saturated ammonium chloride solution was added
13. extractionfollowed by extraction with a mixture of hexane-chloroform (1:1)
14. dry with materialThe organic layer was dried over sodium sulfate
15. filtrationfiltered
16. customThe solvent was then evaporated under reduced pressure
17. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→80:1)