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

HRID 84340

反応式

HRID 84340 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-37878b985dfd4520b897fd0f8ee086da
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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