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

HRID 1463831

反応式

HRID 1463831 の反応式
[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]

参加物

5

反応物 2

HCID 8419VeratraldehydeHCID 75959Pyridine-2-acetonitrile

生成物 1

HCID 3777302-(2-Pyridyl)-3-(3,4-dimethoxy-phenyl)-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 (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°-14 114° C.

後処理

  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

出典と根拠

ORDレコード
ord-2ea6169d125745408d5dee3e129e1601
出典データセット
uspto-grants-1994_04
特許番号
US05302606

関連ノート

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