Reaction #586107

Reaction equation

ammonia

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

water

hydrochloric acid

→

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

Yield 69.3%

Solvents

tetrahydrofuran

Conditions

Workup

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

Procedure

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