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

HRID 1814299Notes

Reaction equation

HRID 1814299 reaction equation
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]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 522689Potassium FluorideHCID 8173215-Bromoquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-57d2c7034a9c4c66b186e7b5d0fbf3e6
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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