Acetone → ethyl 1-benzyl-1H-pyrazole-4-carboxylate

HRID 269798Notes

Reaction equation

HRID 269798 reaction equation
C([C:3]1[C:7]([C:8]([O-:10])=[O:9])=[CH:6][NH:5][N:4]=1)C.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:25][C:26](C)=O>>[CH2:17]([N:4]1[CH:3]=[C:7]([C:8]([O:10][CH2:25][CH3:26])=[O:9])[CH:6]=[N:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178438038HCID 178438038, compound

Product 1

HCID 15237993ethyl 1-benzyl-1H-pyrazole-4-carboxylate

Conditions

Temperature
60 °C

Procedure

To a solution of Ethyl-4-pyrazole-carboxylate (14.0 g, 100 mmol) in Acetone (200 ml) was added potassium carbonate (27.6 g, 200 mmol) and Benzyl Bromide (12 ml, 100 mmol). The mixture was heated to 60° C. and stirred for 14 hours. The reaction mixture was cooled and filtered to remove any solids. The filtrate was concentrated and the residue was purified using column chromatography (3:1 Hexanes:Ethyl Acetate) to yield ethyl 1-benzylpyrazole-4-carboxylate (19.0 g, HNMR)

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customto remove any solids
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified

Sources & evidence

ORD record
ord-46c84bd454b64d45a9a1b7ededd17c2b
Source dataset
uspto-grants-2008_11
Patent number
US07449473B2

Reaction notes

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