Ethyl isobutyrylacetate → Ethyl 4-(4-fluorophenyl)-2-isopropylpyrrole-3-carboxylate

HRID 653692Notes

Reaction equation

HRID 653692 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH:2]([CH3:4])[CH3:3].Cl.[NH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=O.C([O-])(=O)C.[Na+].C([O-])(O)=O.[Na+]>O.C(O)(=O)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:1]([CH:2]([CH3:4])[CH3:3])[NH:13][CH:14]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 81583Ethyl isobutyrylacetateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 132906662-Amino-1-(4-fluorophenyl)ethan-1-one hydrochloride

Product 1

HCID 19889902Ethyl 4-(4-fluorophenyl)-2-isopropylpyrrole-3-carboxylateYield 51.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 6.85 g (43.3 mmol) of ethyl isobutyrylacetate, 10.69 g (56.3 mmol) of 2-amino-4'-fluoracetophenone hydrochloride, 16.3 ml of acetic acid, 6.04 g of sodium acetate, and 10.8 ml of water is refluxed for 4 hours. After cooling, the reaction mixture is adjusted to pH 8 with saturated NaHCO3 and extracted with ether. The extract, 8.36 g, is subjected to column chromatography with silica gel, eluting with methylene chloride to give 6.12 g (Yield:51.3%) of the compound 1.

Workup

  1. temperatureis refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washeluting with methylene chloride

Sources & evidence

ORD record
ord-8b5c83b87e6945c3bfaaba623374d81c
Source dataset
uspto-grants-1992_07
Patent number
US05128366

Reaction notes

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