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

HRID 1975674

Reaction equation

HRID 1975674 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 mi), 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 mi) 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%).

Workup

  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 mi)

Sources & evidence

ORD record
ord-c65e6b9c55144c25b6498e8251701bd5
Source dataset
uspto-grants-1994_02
Patent number
US05288719

Linked notes

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