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

HRID 1760067

反応式

HRID 1760067 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-57282727f02d42d793c1cff2cd7b5ad4
出典データセット
uspto-grants-2005_01
特許番号
US06838563B2

関連ノート

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