Reaktion #586106

Reaktionsgleichung

ethyl acetate

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

tetrahydrofuran

phenyllithium

→

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

Ausbeute 57.9%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at this temperature for another one hour
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGwhile stirring
4. 4
   Temperaturit was refluxed for 10 minutes
5. 5
   Temperaturafter it had cooled to room temperature
6. 6
   SonstigeThe aqueous phase was then separated off from the organic phase
7. 7
   Extraktionthe aqueous phase was extracted twice with diethyl ether
8. 8
   Trocknendried 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
    SonstigeThe precipitate which formed
13. 13
    Filtrationwas filtered off
14. 14
    Sonstigedried

Vorschrift

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.

Quelle