Potassium Iodide → 1-Dodec-7-ynyl-3,5-dimethyl-pyridinium iodide

HRID 84324

反応式

HRID 84324 の反応式
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]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1>CC(=O)CC>[I-:14].[CH2:2]([N+:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[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]

参加物

5

反応物 3

HCID 4875Potassium IodideHCID 115653,5-DimethylpyridineHCID 12350912-Chloro-5-dodecyne

生成物 1

HCID 247812521-Dodec-7-ynyl-3,5-dimethyl-pyridinium iodide収率 78%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 3,5-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 3,5-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 (78%). 1HNMR (300 MHz, CDCl3, ppm), 9.06 (s, 2H), 8.00 (s, 1H), 4.86 (t, 3H), 2.48 (s, 3H), 1.98-2.16 (m, 6H), 1.32-1.48 (br, 10H), 0.88 (t, 3H); 13CNMR, 146.12, 141.38, 138.64, 80.43, 79.53, 61.46, 31.70, 31.17, 28.68, 28.07, 25.55, 21.92, 18.57, 18.42, 13.63.

後処理

  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 3,5-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

出典と根拠

ORDレコード
ord-e8b35a5adc1647c7bd588bcf180338f9
出典データセット
uspto-grants-2014_09
特許番号
US08846937B2

関連ノート

読み込み中…