Allyltributylstannane → 5-(2-Propen-1-yl)quinoline

HRID 1814299ノート

反応式

HRID 1814299 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[F-].[K+]>C1(C)C=CC=CC=1>[CH2:14]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)[CH:13]=[CH2:12]

参加物

5

反応物 3

HCID 90628AllyltributylstannaneHCID 522689Potassium FluorideHCID 8173215-Bromoquinoline

生成物 1

HCID 225041105-(2-Propen-1-yl)quinoline収率 95.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5-Bromo-quinoline (5.6 g, 27 mmol) was dissolved in 40 mL toluene. BHT (50 mg) was added, along with allyl tributyl stannane (9.3 mL, 30 mmol), and tetrakis(triphenyl)phospine palladium (600 mg, 0.52 mmol). The reaction was refluxed overnight, then cooled. Potassium fluoride solution (1.0 g, in 18 mL H2O) was added. The reaction was stirred for 3 hours, then filtered. The reaction mixture was concentrated in vacuo. It was chromatographed in 3:1 hexane/ethyl acetate to yield 4.38 g (95%) of 5-allyl-quinoline as a yellow oil. MS (APCI) m/z 170.1 (M+1).

後処理

  1. temperatureThe reaction was refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customIt was chromatographed in 3:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-57d2c7034a9c4c66b186e7b5d0fbf3e6
出典データセット
uspto-grants-2005_04
特許番号
US06875765B2

反応ノート

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