Reaction #586106

Reaction equation

ethyl acetate

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

tetrahydrofuran

phenyllithium

→

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

Yield 57.9%

Solvents

water

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred at this temperature for another one hour
2. 2
   Temperatureto warm to room temperature
3. 3
   workup.STIRRINGwhile stirring
4. 4
   Temperatureit was refluxed for 10 minutes
5. 5
   Temperatureafter it had cooled to room temperature
6. 6
   OtherThe aqueous phase was then separated off from the organic phase
7. 7
   Extractionthe aqueous phase was extracted twice with diethyl ether
8. 8
   Dryingdried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    workup.DISSOLUTIONThe residue was dissolved in 5 ml of toluene
12. 12
    OtherThe precipitate which formed
13. 13
    Filtrationwas filtered off
14. 14
    Otherdried

Procedure

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.

Source