4-Pyridinecarboxaldehyde → 3-Pyridin-4-YL-acrylic acid methyl ester

HRID 248825

反応式

HRID 248825 の反応式
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:25]1[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=1>O1CCCC1>[N:25]1[CH:26]=[CH:27][C:28]([CH:31]=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[CH:29][CH:30]=1

参加物

4

反応物 2

HCID 133894-PyridinecarboxaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

生成物 1

HCID 981633-Pyridin-4-YL-acrylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl (triphenylphosphoranylidene)acetate (3.4 grams) and 4-pyridine-carboxaldehyde (10.00 grams) were refluxed in tetrahydrofuran under nitrogen overnight. The reaction was evaporated in vacuo, and the residue was suspended in hexane (400 mL), heated to boiling on a steam bath for 5 minutes, and filtered through a filter aide. The filter cake was rinsed with hot hexane (2×200 mL), and the rinses and filtrate were combined and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (1500 mL) using 3:7 ethyl acetate:methylene chloride. The resulting waxy solid was suspended in a minimum amount of cyclohexane to yield the product as a white crystalline solid. Yield: 7.06 grams (46%).

後処理

  1. customThe reaction was evaporated in vacuo
  2. temperatureheated
  3. filtrationfiltered through a filter aide
  4. washThe filter cake was rinsed with hot hexane (2×200 mL)
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography through silica gel 60 (1500 mL)

出典と根拠

ORDレコード
ord-1b1d0d55e92040aebd20be6591631478
出典データセット
uspto-grants-1993_05
特許番号
US05212169

関連ノート

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