تفاعل #2308600

معادلة التفاعل

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

المردود 70.3%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   استخلاصextracted twice with ethyl acetate (150 ml)
3. 3
   غسيلwashed with an aqueous solution
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   ترشيحAfter being filtrated under a reduced pressure
6. 6
   تركيزthe filtrate was concentrated under a reduced pressure
7. 7
   أخرىThe residue obtained
8. 8
   أخرىwas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1)

الإجراء التجريبي

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%)

المصدر