4-Pyridinecarboxaldehyde → HCID 54144036, compound

HRID 1756683Notes

Reaction equation

HRID 1756683 reaction equation
[O-]CC.[Na+].[Na].[N:6]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=1.[Br-].[CH3:15][O:16][C:17]([CH:19]=[CH:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:18]>C(O)C>[N:6]1[CH:7]=[CH:8][C:9]([CH:12]=[CH:21][CH:20]=[CH:19][C:17]([O:16][CH3:15])=[O:18])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 133894-PyridinecarboxaldehydeHCID 2723922Sodium ethoxideHCID 3083751(3-Carbomethoxy-2-propenyl)triphenylphosphonium bromideHCID 5360545Sodium

Product 1

HCID 54144036HCID 54144036, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanolic solution of sodium ethoxide prepared from 1.4 g of sodium and 200 ml of ethanol were added 5.36 g of pyridin-4-aldehyde and 27 g of (3-methoxycarbonyl-2-propenyl)triphenylphosphonium bromide and the mixture was allowed to stand at room temperature for 3 days. The solvent was then distilled off under reduced pressure and the residue was dissolved in water and acidified with 10% hydrochloric acid (pH ca. 5). The solution was washed with ethyl acetate and the aqueous layer was made basic (pH ca. 8) with 10% aqueous sodium hydroxide solution and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give 7.0 g of methyl 5-(pyridin-4-yl)-2,4-pentadienoate as oil.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washThe solution was washed with ethyl acetate
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f704ad8f00c646869ef50e62caac91bd
Source dataset
uspto-grants-1995_08
Patent number
US05441967

Reaction notes

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