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

HRID 84334

反応式

HRID 84334 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][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]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=1>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N+:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[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 114173,4-DimethylpyridineHCID 198479361-(4-Bromo-butyl)-4-butyl-benzene

生成物 1

HCID 247809421-[4-(4-Butyl-phenyl)-butyl]-3,4-dimethyl-pyridinium bromide収率 79%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-(4-Bromo-butyl)-4-butyl-benzene (1 mmol) was added to a solution of 3,4-lutidine (3 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 left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (79%). 1HNMR (300 MHz, CDCl3, ppm), 9.20 (s, 1H), 9.03 (d, J=6.3, 1H), 7.72 (d, J=6.3, 1H), 7.00-7.07 (m, 4H), 4.87 (t, J=7.5, 2H), 2.60 (t, J=7.8, 2H), 2.54 (t, J=7.8, 2H), 2.49 (s, 3H), 2.46 (s, 3H), 1.99-2.04 (m, 2H), 1.50-1.66 (m, 4H), 1.28-1.36 (m, 2H), 0.90 (t, J=7.5, 3H). 13CNMR 157.60, 143.56, 141.92, 140.78, 138.40, 128.63, 128.57, 128.47, 61.00, 35.54, 34.98, 34.04, 31.59, 27.96, 22.73, 20.66, 17.36, 14.31.

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. waitleft 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-d8a68bdd13b5412caf5bb80c1a96dda1
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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