反応 #586107

反応方程式

ammonia

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

water

hydrochloric acid

→

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

収率 69.3%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他The aqueous phase was then separated off from the organic phase
2. 2
   抽出the aqueous phase was extracted twice with diethyl ether
3. 3
   乾燥dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   その他The residue obtained in this way
7. 7
   workup.DISTILLATIONwas distilled at 157-170° C.

実験手順

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.

出典