Реакция #586106

Уравнение реакции

ethyl acetate

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

tetrahydrofuran

phenyllithium

→

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

Выход 57.9%

Растворители

water

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred at this temperature for another one hour
2. 2
   Температураto warm to room temperature
3. 3
   workup.STIRRINGwhile stirring
4. 4
   Температураit was refluxed for 10 minutes
5. 5
   Температураafter it had cooled to room temperature
6. 6
   ДругоеThe aqueous phase was then separated off from the organic phase
7. 7
   Экстракцияthe aqueous phase was extracted twice with diethyl ether
8. 8
   Сушкаdried over magnesium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    workup.DISSOLUTIONThe residue was dissolved in 5 ml of toluene
12. 12
    ДругоеThe precipitate which formed
13. 13
    Фильтрацияwas filtered off
14. 14
    Другоеdried

Методика

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.

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