Potassium Carbonate → Diethyl 1-(2-ethoxyethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate

HRID 880419Notes

Reaction equation

HRID 880419 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[NH:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[CH2:29]([O:31][CH2:32][CH2:33]I)[CH3:30]>C(#N)C>[CH2:29]([O:31][CH2:32][CH2:33][N:12]1[C:8]([CH3:7])=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 291171diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylateHCID 138697091-Ethoxy-2-iodoethane

Product 1

HCID 67241145Diethyl 1-(2-ethoxyethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.82 g, 13.3 mmol) was added to a solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylate (1.0 g, 3.32 mmol) and 1-ethoxy-2-iodo-ethane (1.98 g, 9.96 mmol) in acetonitrile (20 mL) and the mixture heated at reflux for 72 h. The inorganic salts were filtered off and the filtrate was concentrated in vacuo to afford diethyl 1-(2-ethoxyethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate (1.25 g, quantitative).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 72 h
  3. filtrationThe inorganic salts were filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cb65dce3cf974d2a8842caa6331fb81f
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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