3-Ethylpyridine → 1-[4-(4-Butyl-phenyl)-but-3-ynyl]-3-ethyl-pyridinium bromide

HRID 84338

Reaction equation

HRID 84338 reaction equation
[Br:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.[CH2:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:17]>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([C:5]#[C:4][CH2:3][CH2:2][N+:20]2[CH:21]=[CH:22][CH:23]=[C:18]([CH2:16][CH3:17])[CH:19]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 108233-EthylpyridineHCID 593163501-(4-Bromo-but-1-ynyl)-4-butyl-benzene

Product 1

HCID 247809501-[4-(4-Butyl-phenyl)-but-3-ynyl]-3-ethyl-pyridinium bromideYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Bromo-but-1-ynyl)-4-butyl-benzene (1 mmol) was added to a solution of 3-ethylpyridine (3 mmol) in acetonitrile, and the solution was 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 ethylpyridine was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (67%). 1HNMR (300 MHz, CDCl3, ppm), 9.43 (d, J=6.0, 1H), 9.41 (s, 1H), 8.25 (d, J=8.1, 1H), 7.96 (dd, J=6.0, J=8.1, 1H), 7.15 (d, J=8.1, 2H), 7.06, d, J=8.1, 2H), 5.26 (t, J=6.0, 2H), 3.26 (t, J=6.0, 2H), 2.90 (q, J=7.5, 2H), 2.56 (t, J=8.1, 2H), 1.49-1.59 (m, 2H), 1.27-1.37 (m, 5H), 0.90 (t, J=7.2, 3H); 13CNMR, 144.65, 144.46, 144.14, 143.65, 142.45, 131.14, 128.30, 127.12, 118.87, 85.88, 82.45, 59.99, 35.45, 33.27, 26.01, 22.85, 22.21, 14.26, 13.88.

Workup

  1. temperaturethe solution was 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 ethylpyridine
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

Sources & evidence

ORD record
ord-ca9ed83b70d64b7f948288205fbd95fa
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Linked notes

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