Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 4-(2-Pyridyl)-4-oxo-2-butenoic acid, methyl ester

HRID 126997

Reaction equation

HRID 126997 reaction equation
[C:1]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH3:4])=[O:2].Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:28]>C1C=CC=CC=1>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:27](=[O:28])[CH:26]=[CH:5][C:1]([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 383842-Bromoacetamidopyridine

Product 1

HCID 867375424-(2-Pyridyl)-4-oxo-2-butenoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 33.4 g of carbomethoxymethylene triphenylphosphine [Helv. Chim. Acta. 40, 1242 (1957)] in 500 ml of dry benzene under nitrogen is treated with 10 g of 2-(bromoacetyl)pyridine and heated at reflux temperature for 2 hours. The reaction mixture is cooled and filtered to remove carbomethoxymethyl triphenylphosphonium bromide. The filtrate, containing triphenylphosphine, is treated with methyl bromoacetate and heated at reflux temperature for 2 hours. Cooling and filtration removes additional phosphonium salt. The filtrate is concentrated in vacuo yielding the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customto remove carbomethoxymethyl triphenylphosphonium bromide
  6. additionThe filtrate, containing triphenylphosphine
  7. additionis treated with methyl bromoacetate
  8. temperatureheated
  9. temperatureat reflux temperature for 2 hours
  10. temperatureCooling
  11. filtrationfiltration
  12. customremoves additional phosphonium salt
  13. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-9a5a6a6380dd44f8a41023491fe93aa0
Source dataset
uspto-grants-1981_03
Patent number
US04254267

Linked notes

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