Ethyl 3-acetyl-4-oxopentanoate → HCID 54280009, compound

HRID 615005Notes

Reaction equation

HRID 615005 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([C:10](=O)[CH3:11])[C:7](=O)[CH3:8])[CH3:2].Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:10]([CH3:11])=[N:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[C:7]=1[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 517045Sodium AcetateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 54280009HCID 54280009, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.3 grams 3,3-diacetyl-propionic acid-ethyl ester, 8.7 grams p-methoxy phenyl-hydrazinehydrochloride, 4.9 grams anhydrous sodium acetate and 90 milliliters ethanol were mixed and the mixture heated to boiling temperature under reflux for 2.5 hours. The reaction mixture was thereafter evaporated and ether added to the residue. The ether phase was extracted with water and the ether evaporated. The crystalline residue was recrystallized twice from a mixture of ethanol and water. 9.2 grams 3,5-dimethyl-1-(p-methoxy phenyl)-pyrazol-4-acetic acid-ethyl ester, melting at 71°-72° C. were obtained, representing a yield of 64%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe reaction mixture was thereafter evaporated
  4. additionether added to the residue
  5. extractionThe ether phase was extracted with water
  6. customthe ether evaporated
  7. customThe crystalline residue was recrystallized twice from a mixture of ethanol and water

Sources & evidence

ORD record
ord-6e0f2e222fba418388b6df8afb4a6bef
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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