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

HRID 2285957Notes

Reaction equation

HRID 2285957 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-hydrazine-hydrochloride, 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 evaporation. 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 evaporation
  7. customThe crystalline residue was recrystallized twice from a mixture of ethanol and water

Sources & evidence

ORD record
ord-d0f4208fab574799be3e0c1b96b313c4
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

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