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

HRID 47833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47833
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.[CH3:17][C:18]1[C:19](=O)[CH2:20][CH2:21][C:22]=1[CH3:23].Cl.N>C1COCC1>[N:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[C:19]2[CH2:20][CH:21]=[C:22]([CH3:23])[C:18]=2[CH3:17])[CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 142702-Cyclopenten-1-one, 2,3-dimethyl-HCID 1401098-BromoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 223521241-(8-Quinolyl)-2,3-dimethylcyclopentadieneAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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

Aufarbeitung

  1. additionwere subsequently added
  2. temperaturethe solution was refluxed for one hour
  3. customThe cooled reaction mixture
  4. extractionThe aqueous phase was extracted with diethyl ether
  5. customthe combined organic phases were dried
  6. distillationDistillation at 150° C./0.05 mbar

Quellen und Nachweise

ORD-Eintrag
ord-f017544e06f04fcd845165beadfa3de0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699948B2

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