تفاعل #329570

معادلة التفاعل

ammonium chloride

n-butyl lithium

4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole

N-methoxy-N-methylacetamide

→

title compound

1-[4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGby stirring at the same temperature for 30 minutes
2. 2
   workup.STIRRINGstirring
3. 3
   درجة الحرارةwas raised to room temperature
4. 4
   أخرىto terminate
5. 5
   أخرىthe reaction
6. 6
   استخلاصfollowed by extraction with ethyl acetate
7. 7
   استخلاصThe combined extract
8. 8
   غسيلwas washed with saturated brine
9. 9
   تجفيفdried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONsubsequently the solvent was distilled off under reduced pressure
11. 11
    أخرىThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=0%→50%)

الإجراء التجريبي

4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole (24.6 g) was dissolved in THF (300 mL), and cooled to −78° C. while stirring under an argon atmosphere. To the present solution was added dropwise n-butyl lithium (2.66 M hexane solution, 28.9 mL) slowly using a syringe, followed by stirring at the same temperature for 30 minutes. Then, N-methoxy-N-methylacetamide (10.5 mL) was added using a syringe, and stirring was continued for 2 hours while the temperature was raised to room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with ethyl acetate. The combined extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=0%→50%) using silica gel column (product name: Hi-Flash Column 5 L, manufactured by Yamazen Corporation) to afford the title compound (11.7 g).

المصدر