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

HRID 47833

反応式

HRID 47833 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 223521241-(8-Quinolyl)-2,3-dimethylcyclopentadiene収率 41.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f017544e06f04fcd845165beadfa3de0
出典データセット
uspto-grants-2004_03
特許番号
US06699948B2

関連ノート

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