반응 #157752

반응 방정식

tert-Butyldimethylchlorosilane

imidazole

3-(4-bromophenoxy)propan-1-ol

ammonium chloride

→

title compound

수율 79.0%

[3-(4-Bromophenoxy)propoxy](tert-butyl)dimethylsilane

수율 79.0%

용매

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   온도cooling
2. 2
   온도cooled
3. 3
   추출followed by extraction with a mixture of hexane-ethyl acetate (1:1)
4. 4
   건조The organic layer was dried over sodium sulfate
5. 5
   여과filtered
6. 6
   기타The solvent was then evaporated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1)
8. 8
   workup.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. 9
   온도cooling
10. 10
    workup.STIRRINGthe mixture was stirred at room temperature for 27 hours
11. 11
    온도cooled
12. 12
    workup.ADDITIONa saturated ammonium chloride solution was added
13. 13
    추출followed by extraction with a mixture of hexane-chloroform (1:1)
14. 14
    건조The organic layer was dried over sodium sulfate
15. 15
    여과filtered
16. 16
    기타The solvent was then evaporated under reduced pressure
17. 17
    기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→80:1)

실험 절차

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)).

출처