Potassium Iodide → 1-Dodec-7-ynyl-2,4-dimethyl-pyridinium iodide

HRID 84323

반응식

HRID 84323 반응식
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][C:17]=1[CH3:23]>CC(=O)CC>[I-:14].[CH2:2]([N+:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[CH3:23])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13]

참가 물질

5

반응물 3

HCID 4875Potassium IodideHCID 79362,4-DimethylpyridineHCID 12350912-Chloro-5-dodecyne

생성물 1

HCID 247812501-Dodec-7-ynyl-2,4-dimethyl-pyridinium iodide수율 84%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 2,4-lutidine (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 2,4-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 (84%). 1HNMR (300 MHz, CDCl3, ppm), 9.40 (d, 1H), 7.75 (d, 1H), 7.66 (s, 1H), 4.78 (t, 3H), 2.88 (s, 3H), 2.60 (s, 3H), 2.05-2.15 (br, 4H), 1.80-2.00 (br, 2H), 1.30-1.50 (br, 10H), 0.86 (t, 3H); 13CNMR, 156.73, 153.05, 145.84, 136.61, 127.27, 80.86, 79.85, 58.12, 31.54, 30.94, 39.09, 26.17, 22.39, 22.30, 21.03, 18.96, 18.79, 14.02.

후처리

  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 2,4-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

출처 및 근거

ORD 기록
ord-78cdc0c3a89046eb95004dcc3b89588b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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