Potassium Iodide → 1-Dodec-7-ynyl-4-methyl-pyridinium iodide

HRID 84322

Reaktionsgleichung

Reaktionsgleichung von HRID 84322
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].[K+].[N:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1>CC(=O)CC>[I-:14].[CH2:2]([N+:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][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 4875Potassium IodideHCID 79634-MethylpyridineHCID 12350912-Chloro-5-dodecyne

Produkt 1

HCID 247812481-Dodec-7-ynyl-4-methyl-pyridinium iodideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 4-picoline (3 mmol) in butanone. The mixture was refluxed for 3 days and cooled to room temperature, filtrated. The butanone was removed in a vacuum, and the resulting residue was partitioned between water and ethyl ether. The aqueous layer was washed extensively with ether until no 4-picoline 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 (87%). 1HNMR (300 MHz, CDCl3, ppm), 9.28 (d, 2H), 7.92 (d, 2H), 4.92 (t, 2H), 2.68 (s, 3H), 1.96-2.18 (m, 6H), 1.32-1.50 (br, 10H), 0.88 (t, 3H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 days
  2. filtrationfiltrated
  3. customThe butanone was removed in a vacuum
  4. customthe resulting residue was partitioned between water and ethyl ether
  5. washThe aqueous layer was washed extensively with ether until no 4-picoline
  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-b0bfcadd460f456794c4379eb17c286d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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