Реакция #586105

Уравнение реакции

2-methyl-3-(trimethylsilyloxy)cyclopent-2-enone

ammonia

n-butyllithium

hydrochloric acid

8-bromoquinoline

→

2-methyl-3-(8-quinolyl)cyclopent-2-enone

Выход 74.9%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for a further 15 minutes
2. 2
   workup.STIRRINGwhile stirring
3. 3
   Температураto warm to room temperature
4. 4
   workup.STIRRINGwhile stirring
5. 5
   workup.STIRRINGwas stirred for a further one hour
6. 6
   Другоеthe mixture obtained in this way
7. 7
   Температураwas refluxed for 3 hours
8. 8
   Температураto cool to room temperature
9. 9
   workup.STIRRINGwhile stirring
10. 10
    ДругоеThe aqueous phase was then separated off from the organic phase
11. 11
    Экстракцияthe aqueous phase was extracted twice with diethyl ether
12. 12
    Сушкаdried over magnesium sulfate
13. 13
    Фильтрацияfiltered
14. 14
    workup.DISTILLATIONthe solvent was distilled off
15. 15
    ДругоеThe residue obtained in this way
16. 16
    workup.DISTILLATIONwas distilled at 119-139° C.

Методика

A mixture of 38.7 g (186 mmol) of 8-bromoquinoline in 250 ml of tetrahydrofuran was cooled to −80° C. and 74.4 ml of n-butyllithium (2.5 M in hexane, 186 mmol) were subsequently added while stirring. The mixture was stirred for a further 15 minutes and, while stirring, 49.9 g (186 mmol) of 2-methyl-3-(trimethylsilyloxy)cyclopent-2-enone were added. The mixture was allowed to warm to room temperature while stirring and was stirred for a further one hour. The reaction mixture was then hydrolyzed by means of a mixture of 40 g of ice and 30 ml of concentrated hydrochloric acid and the mixture obtained in this way was refluxed for 3 hours. The mixture was allowed to cool to room temperature while stirring and ammonia solution was 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 119-139° C. and 2×10−2 mbar to give 31.1 g (139.3 mmol, 74.9%) of 2-methyl-3-(8-quinolyl)cyclopent-2-enone.

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