تفاعل #329560

معادلة التفاعل

n-butyl lithium

ammonium chloride

( 2 )

4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-1H-imidazole

N-methoxy-N-methylacetamide

→

title compound

1-[4-(tert-Butyldiphenylsilyloxymethyl)-1-vinyl-1H-imidazol-2-yl]ethanone

1-[4-(tert-butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-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
   أخرىwas gradually brought back to room temperature
4. 4
   أخرىto terminate
5. 5
   أخرىthe reaction
6. 6
   استخلاصfollowed by extraction with ethyl acetate
7. 7
   غسيلThe extract was washed with saturated brine
8. 8
   تجفيفdried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONsubsequently the solvent was distilled off under reduced pressure
10. 10
    أخرىThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=4%→40%)

الإجراء التجريبي

The compound (5.35 g) obtained in (2) was dissolved in THF (200 mL), and cooled to −78° C. while stirring under nitrogen stream. To the present solution was added dropwise n-butyl lithium (2.76 M hexane solution, 7.60 mL), followed by stirring at the same temperature for 30 minutes. Then, N-methoxy-N-methylacetamide (2.91 mL) was added, and stirring was continued for 4 hours while the temperature was gradually brought back 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 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=4%→40%) using silica gel column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (1.48 g) and 1-[4-(tert-butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-1H-imidazol-2-yl)ethanone (3.91 g).

المصدر