Hydrochloric Acid → 1-(8-Quinolyl)-indan-1-ol

HRID 47834

反応式

HRID 47834 の反応式
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Li]CCCC.[C:17]1(=[O:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18]1.Cl>C1COCC1>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[C:17]2([OH:26])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18]2)[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 1401098-BromoquinolineHCID 178418339Butyllithium

生成物 1

HCID 223521191-(8-Quinolyl)-indan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-100 °C

実験手順

8-Bromoquinoline (10.4 g, 50 mmol) was introduced into 100 ml of THF, and the mixture was cooled to about −100° C. 20 ml of n-BuLi (2.5 M in hexane, 50 mmol) were added dropwise, during which the internal temperature was kept below −80° C. When the addition was complete, the mixture was stirred at −80° C. for a further 15 minutes, and 6.6 g of 1-indanone (50 mmol), dissolved in 30 ml of THF, were then added dropwise. The reaction mixture was then allowed to warm slowly to room temperature, and was then refluxed for 3 hours. After the mixture had cooled to room temperature, firstly ice and then hydrochloric acid were added to about pH 1, and the mixture was stirred for 30 minutes. The aqueous and organic phases were separated, the aqueous phase was treated with ammonia solution to about pH 9 and extractetd with ether, and the combined organic phases were subsequently evaporated to dryness under reduced pressure. The viscous oil obtained in this way (1-(8-quinolyl)-indan-1-ol (8H2O)) was treated with hydrochloric acid to pH 0, refluxed for 2 hours and subsequently neutralized. After work-up and drying, 6.6 g of 1-(8-quinolyl)indene (55%) were isolated as a colorless solid.

後処理

  1. customwas kept below −80° C
  2. additionWhen the addition
  3. additionwere then added dropwise
  4. temperatureto warm slowly to room temperature
  5. temperaturewas then refluxed for 3 hours
  6. temperatureAfter the mixture had cooled to room temperature
  7. stirringthe mixture was stirred for 30 minutes
  8. customThe aqueous and organic phases were separated
  9. additionthe aqueous phase was treated with ammonia solution to about pH 9 and extractetd with ether
  10. customthe combined organic phases were subsequently evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-c5b806c595564815b798cc8f0e10df12
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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