Reacción #2308600

Ecuación de reacción

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

Rendimiento 70.3%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Extracciónextracted twice with ethyl acetate (150 ml)
3. 3
   Lavadowashed with an aqueous solution
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   FiltraciónAfter being filtrated under a reduced pressure
6. 6
   Concentraciónthe filtrate was concentrated under a reduced pressure
7. 7
   OtroThe residue obtained
8. 8
   Otrowas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1)

Procedimiento

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%)

Fuente