Sodium Iodide → 1-Dodec-7-ynyl-3,4-dimethyl-pyridinium iodide

HRID 84325

Reaktionsgleichung

Reaktionsgleichung von HRID 84325
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13].[I-:14].[Na+].[N:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1>CC(=O)CC>[I-:14].[CH2:2]([N+:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 114173,4-DimethylpyridineHCID 12350912-Chloro-5-dodecyne

Produkt 1

HCID 247812541-Dodec-7-ynyl-3,4-dimethyl-pyridinium iodideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

12-Chloro-dodec-5-yne (1 mmol) was mixed with Sodium iodide (3 mmol) and 3,4-lutidine (3 mmol) in butanone. The mixture was refluxed for 3 days and cooled to room temperature, filtrated. The butanone was removed in vacuum, and the resulting residue was partitioned between water and ethyl ether. The aqueous layer was washed extensively with ether until no 3,4-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 (72%). 1HNMR, (300 MHz, CDCl3, ppm, ppm), 9.22 (s, 1H), 9.04 (d, 1H), 7.80 (d, 1H), 4.84 (t, 3H), 2.52 (s, 3H), 2.50 (s, 3H), 1.92-2.14 (m, 6H), 1.28-1.45 (m, 10H), 0.84 (t, 3H). 13CNMR, 157.84, 143.39, 141.81, 138.53, 128.72, 80.80, 79.90, 61.23, 32.03, 31.54, 29.08, 28.48, 25.91, 22.30, 20.78, 18.96, 18.79, 17.44, 14.02.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 days
  2. filtrationfiltrated
  3. customThe butanone was removed in vacuum
  4. customthe resulting residue was partitioned between water and ethyl ether
  5. washThe aqueous layer was washed extensively with ether until no 3,4-lutidine
  6. waitwas left in the aqueous layer
  7. extractionThe resulting aqueous solution of the product was extracted with chloroform
  8. customThe chloroform was removed

Quellen und Nachweise

ORD-Eintrag
ord-5e891cc7ab8f4e1186ceef63d022a235
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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