3-Methylpyridine → 1-[4-(4-Butyl-phenyl)-but-3-ynyl]-3-methyl-pyridinium bromide

HRID 84336ノート

反応式

HRID 84336 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]=[CH:20][CH:19]=[C:18]([CH3:22])[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]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

参加物

4

反応物 2

HCID 79703-MethylpyridineHCID 593163501-(4-Bromo-but-1-ynyl)-4-butyl-benzene

生成物 1

HCID 685930501-[4-(4-Butyl-phenyl)-but-3-ynyl]-3-methyl-pyridinium bromide収率 77%

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-picoline (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 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 (77%). 1HNMR R (300 MHz, CDCl3, ppm), 9.48 (s, 1H), 9.33 (d, J=6.6, 1H), 8.24 (d, J=7.2, 1H), 7.93 (dd, J=6.6, J=7.2, 1H), 7.16 (d, J=8.2, 2H), 7.06 (d, J=8.2, 2H), 5.21 (t, J=6.0, 2H), 3.26 (t, J=6.0, 2H), 2.59 (s, 3H), 2.56 (t, 2H), 1.49-1.59 (m 2H), 1.25-1.37 (m, 2H), 0.9 (t, J=7.2, 3H); 13CNMR, 145.70, 144.78, 143.64, 142.26, 138.98, 131.15, 128.32, 126.94, 118.92, 85.84, 82.45, 59.90, 35.45, 33.28, 22.81. 22.24, 18.71, 13.89.

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 picoline
  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-91408534a8954b77873ae93098f13ab1
出典データセット
uspto-grants-2014_09
特許番号
US08846937B2

反応ノート

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