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

HRID 1814299노트

반응식

HRID 1814299 반응식
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]

참가 물질

5

반응물 3

HCID 90628AllyltributylstannaneHCID 522689Potassium FluorideHCID 8173215-Bromoquinoline

생성물 1

HCID 225041105-(2-Propen-1-yl)quinoline수율 95.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-57d2c7034a9c4c66b186e7b5d0fbf3e6
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

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