Ammonia → 1-(8-Quinolyl)-2,3-dimethylcyclopentadiene

Beteiligte Stoffe

Reaktionsschritte

5 ml of n-BuLi (2.5 M in hexane, 12.5 mmol) were added at −95° C. dropwise to a solution of 2.5 g of 8-bromoquinoline (12 mmol) in 120 ml of THF; this was stirred for 15 minutes, and then 1.3 g of 2,3-dimethylcyclopent-2-enone (12 mmol), dissolved in 10 ml of THF, was added. After warming to room temperature, the solution was heated for one hour in ref lux. The cooled reaction mixture was hydrolized with ice, acidified with hydrochloric acid, and then neutralized with ammonia solution. The aqueous phase was extracted with diethyl ether, and the combined organic phases were dried. Distillation at 150° C. and 0.05 mbar yielded 1.1 g of 1-(8-quinolyl)-2,3-dimethylcyclopentadiene (40%) in the form of a yellow, viscous oil.

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