3-Ethylpyridine → 1-[4-(4-Butyl-phenyl)-but-3-ynyl]-3-ethyl-pyridinium bromide

HRID 84338

反応式

HRID 84338 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.[CH2:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:17]>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+:20]2[CH:21]=[CH:22][CH:23]=[C:18]([CH2:16][CH3:17])[CH:19]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

参加物

4

反応物 2

HCID 108233-EthylpyridineHCID 593163501-(4-Bromo-but-1-ynyl)-4-butyl-benzene

生成物 1

HCID 247809501-[4-(4-Butyl-phenyl)-but-3-ynyl]-3-ethyl-pyridinium bromide収率 67%

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-ethylpyridine (3 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no ethylpyridine 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 (67%). 1HNMR (300 MHz, CDCl3, ppm), 9.43 (d, J=6.0, 1H), 9.41 (s, 1H), 8.25 (d, J=8.1, 1H), 7.96 (dd, J=6.0, J=8.1, 1H), 7.15 (d, J=8.1, 2H), 7.06, d, J=8.1, 2H), 5.26 (t, J=6.0, 2H), 3.26 (t, J=6.0, 2H), 2.90 (q, J=7.5, 2H), 2.56 (t, J=8.1, 2H), 1.49-1.59 (m, 2H), 1.27-1.37 (m, 5H), 0.90 (t, J=7.2, 3H); 13CNMR, 144.65, 144.46, 144.14, 143.65, 142.45, 131.14, 128.30, 127.12, 118.87, 85.88, 82.45, 59.99, 35.45, 33.27, 26.01, 22.85, 22.21, 14.26, 13.88.

後処理

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no ethylpyridine
  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-ca9ed83b70d64b7f948288205fbd95fa
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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