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

HRID 235044

반응식

HRID 235044 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08a056f471524fe5ba1ae4ecc0082ddb
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597837

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