Réaction #586107

Équation de réaction

ammonia

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

water

hydrochloric acid

→

2-methyl-3-phenyl-1-(8-quinolyl)cyclopentadiene

Rendement 69.3%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreThe aqueous phase was then separated off from the organic phase
2. 2
   Extractionthe aqueous phase was extracted twice with diethyl ether
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   AutreThe residue obtained in this way
7. 7
   workup.DISTILLATIONwas distilled at 157-170° C.

Mode opératoire

A mixture of 5 ml of water and 5 ml of concentrated hydrochloric acid was added to a solution of 1.717 g (5.7 mmol) of 3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene in 100 ml of tetrahydrofuran. The mixture was stirred at room temperature for 90 minutes and ammonia solution was then added until the pH was 12. 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 obtained in this way was distilled at 157-170° C. and 2×10−2 mbar to give 1.12 g (3.95 mmol, 69.3%) of 2-methyl-3-phenyl-1-(8-quinolyl)cyclopentadiene.

Source