3,5-Dimethylpyridine → 1-[4-(4-Butyl-phenyl)-but-3-ynyl]-3,5-dimethyl-pyridinium bromide

HRID 84340

Reaktionsgleichung

Reaktionsgleichung von HRID 84340
[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.[N:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1>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+:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 115653,5-DimethylpyridineHCID 593163501-(4-Bromo-but-1-ynyl)-4-butyl-benzene

Produkt 1

HCID 247810971-[4-(4-Butyl-phenyl)-but-3-ynyl]-3,5-dimethyl-pyridinium bromideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-(4-Bromo-but-1-ynyl)-4-butyl-benzene (1 mmol) was added to a solution of 3,5-lutidine (2 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in a vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no lutidine 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 (80%). 1HNMR (300 MHz, CDCl3, ppm), 9.39 (s, 1H), 9.13 (d, J=6.3, 1H), 7.70 (d, J=6.3, 1H), 7.17 (d, J=8.1, 2H), 7.07 (d, J=8.1, 2H), 5.13 (t, J=6.0, 2H), 3.23 (t, J=6.0, 2H), 2.57 (t, J=7.8, 2H), 2.53 (s, 3H), 2.48 (s, 3H), 1.50-1.58 (m, 2H), 1.28-1.37 (m, 2H), 0.90 (t, J=7.2, 3H); 13CNMR, 158.19, 143.98, 138.11, 131.53, 128.69, 128.05, 119.45, 83.11, 59.60, 35.84, 33.64, 23.12, 22.62, 20.77, 17.35, 14.23.

Aufarbeitung

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in a vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no lutidine
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

Quellen und Nachweise

ORD-Eintrag
ord-37878b985dfd4520b897fd0f8ee086da
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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