2-Propynoic acid, 3-phenyl-, ethyl ester → 4-Ethoxycarbonyl-1-(2-cyanoethyl)-3-phenylpyrrole

HRID 1607911Notes

Reaction equation

HRID 1607911 reaction equation
[CH2:1]([O:3][C:4]([C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[CH3:2].[C:14]([CH2:16][CH2:17][N:18]([CH:23]=O)[CH2:19]C(O)=O)#[N:15]>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][N:18]([CH2:17][CH2:16][C:14]#[N:15])[CH:23]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 19849818N-(2-Cyanoethyl)-N-formylglycine

Product 1

HCID 198498214-Ethoxycarbonyl-1-(2-cyanoethyl)-3-phenylpyrrole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

17.4 g of phenylacetylenecarboxylic acid ethyl ester and 15.6 g of N-(2-cyanoethyl)-N-formylglycine are dissolved in 100 ml of acetic anhydride, and the solution is refluxed for 24 h. The mixture is concentrated by evaporation under reduced pressure; the residue is then taken up in toluene, and purified by chromatography through silica gel. The solvent is evaporated off, and from the eluate is obtained 4-ethoxycarbonyl-1-(2-cyanoethyl)-3-phenylpyrrole in the form of a yellow oil (compound No. 3.3).

Workup

  1. temperaturethe solution is refluxed for 24 h
  2. concentrationThe mixture is concentrated by evaporation under reduced pressure
  3. custompurified by chromatography through silica gel
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-bc42836ad0764d46add67310c3faf3e3
Source dataset
uspto-grants-1989_09
Patent number
US04868202

Reaction notes

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