반응 #586106

반응 방정식

ethyl acetate

2-methyl-3-(8-quinolyl)cyclopent-2-enone

tetrahydrofuran

phenyllithium

→

3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene

수율 57.9%

용매

water

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at this temperature for another one hour
2. 2
   온도to warm to room temperature
3. 3
   workup.STIRRINGwhile stirring
4. 4
   온도it was refluxed for 10 minutes
5. 5
   온도after it had cooled to room temperature
6. 6
   기타The aqueous phase was then separated off from the organic phase
7. 7
   추출the aqueous phase was extracted twice with diethyl ether
8. 8
   건조dried over magnesium sulfate
9. 9
   여과filtered
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    workup.DISSOLUTIONThe residue was dissolved in 5 ml of toluene
12. 12
    기타The precipitate which formed
13. 13
    여과was filtered off
14. 14
    기타dried

실험 절차

A mixture of 2.4 g (10.75 mmol) of 2-methyl-3-(8-quinolyl)cyclopent-2-enone with 100 ml of tetrahydrofuran was cooled to −90° C. and 7.2 ml of phenyllithium (1.8 M in cyclohexane/diethyl ether, 12.9 mmol) were subsequently added while stirring. The mixture was stirred at this temperature for another one hour and 1 ml of ethyl acetate was then added. The mixture was then allowed to warm to room temperature while stirring, it was refluxed for 10 minutes and, after it had cooled to room temperature, 100 ml of water were added. The aqueous phase was then separated off from the organic phase and the aqueous phase was extracted twice with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and the solvent was distilled off. The residue was dissolved in 5 ml of toluene and then admixed with 80 ml of hexane. The precipitate which formed was filtered off and dried. This gave 1.874 g (6.22 mmol, 57.9% yield) of 3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene.

출처