4-Methylpyridine → HCID 24742480, compound

HRID 1925444Notes

Reaction equation

HRID 1925444 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13]Br.[N:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1>C(#N)C>[Br-:1].[Br-:1].[CH2:2]([N+:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][N+:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 58338516HCID 58338516, compound

Product 1

HCID 24742480HCID 24742480, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis-cis-1,12-Dibromo-dodeca-5,7-diene was added to a solution of 4-picoline (3 mmol) in acetonitrile and the solution refluxed for 24 hours. The acetonitrile was removed in vacuum and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no picoline left in the aqueous layer The resulting aqueous solution of the product was lyophilized to yield the pure product. (75%). 1HNMR (300 MHz, D2O, ppm), 8.45 (d, J=6.9, 4H), 7.68 (d, J=6.9, 4H), 6.14-6.19 (m, 2H), 5.31-5.39 (m, 2H), 4.35 (t, J=7.2, 4H), 2.47 (s, 6H), 2.07 (q, J=7.2, 4H), 1.83 (p, J=7.5, 4H), 1.25 (p, J=7.5, 4H).

Workup

  1. temperaturethe solution refluxed for 24 hours
  2. customThe acetonitrile was removed in vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no picoline
  5. waitleft in the aqueous layer The resulting aqueous solution of the product
  6. customto yield the pure product

Sources & evidence

ORD record
ord-04f9571f1d6c4fccbb73f0a0fe20ecb7
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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