Potassium Iodide → 1-Dodec-7-ynyl-3-methyl-pyridinium iodide

HRID 84321

反応式

HRID 84321 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]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1>CC(=O)CC>[I-:14].[CH2:2]([N+:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[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 79703-MethylpyridineHCID 12350912-Chloro-5-dodecyne

生成物 1

HCID 247812461-Dodec-7-ynyl-3-methyl-pyridinium iodide収率 82%

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-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 3-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 (82%). 1HNMR (300 MHz, CDCl3, ppm) 9.36 (s, 1H), 9.18 (d, 1H), 8.24 (d, 1H), 8.00 (dd, 1H), 4.92 (t, 2H), 2.62 (s, 3H), 1.95-2.18 (m, 6H), 1.15-1.25 (br, 10H), 0.90 (t, 3H); 13CNMR, 145.51, 144.12, 144.78, 139.46, 127.56, 80.44, 79.42, 61.75, 31.72, 31.16, 28.65, 28.04, 25.52, 21.92, 18.75, 18.55, 18.40, 13.63.

後処理

  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 3-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

出典と根拠

ORDレコード
ord-df32e401b2eb4e03992f93faec91949f
出典データセット
uspto-grants-2014_09
特許番号
US08846937B2

関連ノート

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