Pyrrole-2-carboxaldehyde → Methyl 3-(1H-pyrrol-2-yl)propanoate

HRID 327788Notes

Reaction equation

HRID 327788 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[C:8]([CH:12]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:10][CH3:11])=[O:9]>C1C=CC=CC=1>[CH3:11][O:10][C:8]([CH2:12][CH2:6][C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:9]

Participants

4

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 14668764Methyl 3-(1H-pyrrol-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The 2-(2-methoxycarbonylethyl)pyrrole is prepared as follows: A solution of pyrrole-2-carboxaldehyde (3.9 g, 41 mmol) and (carbomethoxymethylene)-triphenylphosphorane (14 g, 42 mmol) in 160 mL of dry benzene is heated at reflux for 18 hours under a nitrogen atmosphere. After cooling, the reaction mixture is concentrated under vacuum and the resulting oil is purified by silica gel column chromatography, eluting with a mixture of ethyl acetate and hexane (1:9) to give 5.11 g of a mixture of cis- and trans-methyl 2-(2-pyrrolyl)acrylate.

Workup

  1. temperatureat reflux for 18 hours under a nitrogen atmosphere
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated under vacuum
  4. customthe resulting oil is purified by silica gel column chromatography
  5. washeluting with a mixture of ethyl acetate and hexane (1:9)

Sources & evidence

ORD record
ord-2f067e668de64e4aaf54fbb97d1f90d8
Source dataset
uspto-grants-1993_12
Patent number
US05274113

Reaction notes

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