反应 #586106

反应方程式

ethyl acetate

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

tetrahydrofuran

phenyllithium

→

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

收率 57.9%

溶剂

water

反应条件

后处理

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
   其他The aqueous phase was then separated off from the organic phase
7. 7
   萃取the aqueous phase was extracted twice with diethyl ether
8. 8
   干燥dried over magnesium sulfate
9. 9
   过滤filtered
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    workup.DISSOLUTIONThe residue was dissolved in 5 ml of toluene
12. 12
    其他The precipitate which formed
13. 13
    过滤was filtered off
14. 14
    其他dried

实验过程

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.

来源