Pyridine-2-acetonitrile → 2-(2-Pyridyl)-3-(3,5-di-tert-butylphenyl)-2-propenenitrile

HRID 235044

反応式

HRID 235044 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]#[N:25]>C(O)C.N1CCCCC1>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:8][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=1)[C:24]#[N:25]

参加物

5

反応物 2

HCID 75959Pyridine-2-acetonitrileHCID 12682533,5-Bis(tert-butyl)benzaldehyde

生成物 1

HCID 537161712-(2-Pyridyl)-3-(3,5-di-tert-butylphenyl)-2-propenenitrile

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 702Ethanol溶媒

実験手順

To a stirred solution of 2.0 g (9.17 mmole) 3,5-di-tertbutylbenzaldehyde in 75 ml absolute ethanol are added 1.19 g (10.1 mmole) 2-pyridylacetonitrile and 12 drops piperidine. The reaction flask is equipped with a condenser and a drying tube (using anhydrous CaSO4), and the reaction is stirred and heated. After refluxing for 8 hours, the reaction is allowed to cool to room temperature and stirred overnight for 16 hours. The solvent is removed by rotary evaporation, and the residue purified by flash chromatography on silica gel, eluting with hexane-ethyl acetate, 98:2. The colorless solid is washed with cold ether-hexane to give 2-(2-pyridyl)-3-(3,5-di-tert-butylphenyl)-2-propenenitrile, m.p. 90°-93° C.

後処理

  1. temperatureheated
  2. temperatureAfter refluxing for 8 hours
  3. stirringstirred overnight for 16 hours
  4. customThe solvent is removed by rotary evaporation
  5. customthe residue purified by flash chromatography on silica gel
  6. washeluting with hexane-ethyl acetate, 98:2
  7. washThe colorless solid is washed with cold ether-hexane

出典と根拠

ORDレコード
ord-08a056f471524fe5ba1ae4ecc0082ddb
出典データセット
uspto-grants-1997_01
特許番号
US05597837

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