Ethyl isobutyrylacetate → HCID 69052716, compound

HRID 1246105Notes

Reaction equation

HRID 1246105 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[CH:13]([CH3:15])[CH3:14].C([O-])(=O)C.[Na+]>O>[CH2:21]([O:20][C:18]([C:17]1[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:3][NH:2][C:12]=1[CH:13]([CH3:15])[CH3:14])=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 81583Ethyl isobutyrylacetateHCID 517045Sodium AcetateHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

Product 1

HCID 69052716HCID 69052716, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-aminoacetophenone hydrochloride (1 equiv.), ethyl isobutyrylacetate (1.2 equiv.) and sodium acetate (2.4 equiv.) in H2O was stirred at 100° C. for 18 hours and then cooled to room temperature. The aqueous layer was decanted off and the oil was dissolved in ethyl acetate. It was then washed with water and brine and then dried to give (93%) of 2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester as a red brown oil.

Workup

  1. temperaturecooled to room temperature
  2. customThe aqueous layer was decanted off
  3. dissolutionthe oil was dissolved in ethyl acetate
  4. washIt was then washed with water and brine
  5. customdried

Sources & evidence

ORD record
ord-65e099be22cf4653af6d87f94a1b4793
Source dataset
uspto-grants-2006_10
Patent number
US07125905B2

Reaction notes

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