反応 #76115

反応方程式

hydrochloric acid

8-bromo-2-methylquinoline

n-BuLi

ammonia

2,3,4,5-tetramethylcyclopentenone

→

1-(2-Methyl-8-quinolyl)-2,3,4,5-tetramethylcyclopentadiene

収率 60.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGAfter the mixture had been stirred for 10 minutes
2. 2
   温度refluxed for one hour
3. 3
   温度cooled
4. 4
   その他the phases were separated
5. 5
   抽出the aqueous phase was extracted with pentane
6. 6
   その他After the combined organic extracts had been dried
7. 7
   その他the pentane was removed under reduced pressure
8. 8
   workup.DISTILLATIONthe brown oil which remained was distilled under a high vacuum (b.p.: 115° C./0.01 mbar)

実験手順

A solution of 4.4 q of 8-bromo-2-methylquinoline (20 mmol) in 50 ml of THF was cooled to −78° C., and 8.8 ml of n-BuLi (2.5 M in hexane, 22 mmol) were added dropwise with stirring. After the mixture had been stirred for 10 minutes, 3.5 g of 2,3,4,5-tetramethylcyclopentenone (25 mmol) were added dropwise, and the solution was warmed to room temperature, refluxed for one hour and cooled. Ice and hydrochloric acid were added to about pH 1, the mixture was neutralized using ammonia solution, the phases were separated, and the aqueous phase was extracted with pentane. After the combined organic extracts had been dried, the pentane was removed under reduced pressure, and the brown oil which remained was distilled under a high vacuum (b.p.: 115° C./0.01 mbar). 1-(2-Methyl-8-quinolyl)-2,3,4,5-tetramethylcyclopentadiene was obtained as a yellow, viscous oil in a yield of 60% (3.2 g).

出典