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

HRID 1760067

Reaktionsgleichung

Reaktionsgleichung von HRID 1760067
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[Li]CCCC.[CH3:18][C:19]1[C:20](=O)[CH:21]([CH3:26])[CH:22]([CH3:25])[C:23]=1[CH3:24].Cl.N>C1COCC1>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([C:20]3[CH:19]([CH3:18])[C:23]([CH3:24])=[C:22]([CH3:25])[C:21]=3[CH3:26])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 410922,3,4,5-Tetramethyl-2-cyclopentenoneHCID 47150308-Bromo-2-methylquinolineHCID 178418339Butyllithium

Produkt 1

HCID 223521291-(2-Methyl-8-quinolyl)-2,3,4,5-tetramethylcyclopentadieneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4.4 g 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).

Aufarbeitung

  1. stirringAfter the mixture had been stirred for 10 minutes
  2. temperaturerefluxed for one hour
  3. temperaturecooled
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted with pentane
  6. customAfter the combined organic extracts had been dried
  7. customthe pentane was removed under reduced pressure
  8. distillationthe brown oil which remained was distilled under a high vacuum (b.p.: 115° C./0.01 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-57282727f02d42d793c1cff2cd7b5ad4
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838563B2

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