Ethyl Acrylate → Ethyl 1-(3-ethoxy-3-oxopropyl)-4-phenylpyrrole-2-carboxylate

HRID 880439Notes

Reaction equation

HRID 880439 reaction equation
CC(C)([O-])C.[K+].[C:7]1([C:13]2[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[CH:24]=[CH2:25]>C(O)(=O)C>[CH2:28]([O:27][C:23](=[O:26])[CH2:24][CH2:25][N:16]1[CH:17]=[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=[C:15]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:29]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66914703Ethyl 1-(3-ethoxy-3-oxopropyl)-4-phenylpyrrole-2-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium tert-butoxide (100 mg, 0.90 mmol), ethyl 4-phenyl-1H-pyrrole-2-carboxylate (1.0 g, 4.65 mmol) and ethyl acrylate (50 mL) were heated at reflux for 90 min. The reaction mixture was allowed to cool to room temperature and neutralized with acetic acid (1 mL). Excess ethyl acrylate was evaporated in vacuo, the residue diluted with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude compound. Purification by column chromatography over neutral alumina using 5% ethyl acetate in petroleum ether as eluent gave ethyl 1-(3-ethoxy-3-oxo-propyl)-4-phenyl-pyrrole-2-carboxylate (1.0 g, 69%) as an oil.

Workup

  1. temperatureat reflux for 90 min
  2. customExcess ethyl acrylate was evaporated in vacuo
  3. additionthe residue diluted with water
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude compound
  9. customPurification by column chromatography over neutral alumina using 5% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-b7171df2364e49f0b2876d8234000ba7
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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