3,5-Dimethylpyridine → 1-[4-(4-Butyl-phenyl)-but-3-ynyl]-3,5-dimethyl-pyridinium bromide

HRID 84340

반응식

HRID 84340 반응식
[Br:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.[N:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([C:5]#[C:4][CH2:3][CH2:2][N+:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

참가 물질

4

반응물 2

HCID 115653,5-DimethylpyridineHCID 593163501-(4-Bromo-but-1-ynyl)-4-butyl-benzene

생성물 1

HCID 247810971-[4-(4-Butyl-phenyl)-but-3-ynyl]-3,5-dimethyl-pyridinium bromide수율 80%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-(4-Bromo-but-1-ynyl)-4-butyl-benzene (1 mmol) was added to a solution of 3,5-lutidine (2 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in a vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no 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 (80%). 1HNMR (300 MHz, CDCl3, ppm), 9.39 (s, 1H), 9.13 (d, J=6.3, 1H), 7.70 (d, J=6.3, 1H), 7.17 (d, J=8.1, 2H), 7.07 (d, J=8.1, 2H), 5.13 (t, J=6.0, 2H), 3.23 (t, J=6.0, 2H), 2.57 (t, J=7.8, 2H), 2.53 (s, 3H), 2.48 (s, 3H), 1.50-1.58 (m, 2H), 1.28-1.37 (m, 2H), 0.90 (t, J=7.2, 3H); 13CNMR, 158.19, 143.98, 138.11, 131.53, 128.69, 128.05, 119.45, 83.11, 59.60, 35.84, 33.64, 23.12, 22.62, 20.77, 17.35, 14.23.

후처리

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in a vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no lutidine
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

출처 및 근거

ORD 기록
ord-37878b985dfd4520b897fd0f8ee086da
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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