Ethyl 2,4-dioxovalerate → Ethyl 1-(4-fluorophenyl)-3-methyl-1H-pyrazole-5-carboxylate

HRID 1744476Notes

Reaction equation

HRID 1744476 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.O=[C:11]([CH2:17][C:18](=O)[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][C:18]([CH3:19])=[N:9]2)=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:18]([CH3:19])=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 69208Ethyl 2,4-dioxovalerateHCID 69982(4-Fluorophenyl)hydrazine

Product 2

HCID 22227950Ethyl 1-(4-fluorophenyl)-3-methyl-1H-pyrazole-5-carboxylateHCID 22228105HCID 22228105, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (30 ml) were added 4-fluorophenylhydrazine (5 g) and ethyl 2,4-dioxovalerate (10.6 g) and the mixture was refluxed for 3 h. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (mobile phase: chloroform) to give ethyl 1-(4-fluorophenyl)-3-methylpyrazole-5-carboxylate (2 g) and ethyl 1-(4-fluorophenyl)-5-methylpyrazole-3-carboxylate (3 g).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (mobile phase: chloroform)

Sources & evidence

ORD record
ord-8aa3a48362384259ad3bfefd3cca0121
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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