反応 #586106

反応方程式

ethyl acetate

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

tetrahydrofuran

phenyllithium

→

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

収率 57.9%

溶媒

water

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at this temperature for another one hour
2. 2
   温度to warm to room temperature
3. 3
   workup.STIRRINGwhile stirring
4. 4
   温度it was refluxed for 10 minutes
5. 5
   温度after it had cooled to room temperature
6. 6
   その他The aqueous phase was then separated off from the organic phase
7. 7
   抽出the aqueous phase was extracted twice with diethyl ether
8. 8
   乾燥dried over magnesium sulfate
9. 9
   ろ過filtered
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    workup.DISSOLUTIONThe residue was dissolved in 5 ml of toluene
12. 12
    その他The precipitate which formed
13. 13
    ろ過was filtered off
14. 14
    その他dried

実験手順

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.

出典