반응 #1245493

반응 방정식

2-Bromo-4-nitroimidazole

1-(tert-butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane

potassium carbonate

sodium iodide

→

2-bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy) propyl]-4-nitroimidazole

수율 70.3%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   추출extracted twice with ethyl acetate (150 ml)
3. 3
   세척washed with an aqueous solution
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과After being filtrated under a reduced pressure
6. 6
   농축the filtrate was concentrated under a reduced pressure
7. 7
   기타The residue obtained
8. 8
   기타was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1)

실험 절차

2-Bromo-4-nitroimidazole (7.63 g) and 1-(tert-butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane (12 g) were dissolved in N,N-dimethylformamide (80 ml), then potassium carbonate (6.6 g) and sodium iodide (6.3 g) were added thereto, and the reaction mixture was heated and stirred at 110° C. for 12 hours. Ice-water (240 ml) was added, extracted twice with ethyl acetate (150 ml), and the extracts were combined together and washed with an aqueous solution being saturated with sodium chloride (100 ml), then dried over anhydrous magnesium sulfate. After being filtrated under a reduced pressure, the filtrate was concentrated under a reduced pressure. The residue obtained was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1), there was obtained 2-bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy) propyl]-4-nitroimidazole (12.69 g, yield: 68.7%).

출처