Veratraldehyde → 2-(2-Pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile

HRID 1489153

반응식

HRID 1489153 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]#[N:21]>C(O)C.N1CCCCC1>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:20]#[N:21]

참가 물질

5

반응물 2

HCID 8419VeratraldehydeHCID 75959Pyridine-2-acetonitrile

생성물 1

HCID 3777302-(2-Pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 702Ethanol용매

실험 절차

To a stirred solution of 2.0 g (12.0 mmole) 3,4-dimethoxybenzaldehyde in 75 ml absolute ethanol are added 1.56 g (13.3 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 6 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, 4:1. The yellow solid is recrystallized from acetone-hexane to give 2-(2-pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile, m.p. 112°-114° C.

후처리

  1. temperatureheated
  2. temperatureAfter refluxing for 6 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, 4:1
  7. customThe yellow solid is recrystallized from acetone-hexane

출처 및 근거

ORD 기록
ord-8f6a3780991b4f058da01d1fc1c29c05
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677329

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