Potassium Carbonate → Ethyl 1-(3-phenylpropyl)pyrazole-4-carboxylate

HRID 18117

Reaction equation

HRID 18117 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[C:21]1([CH2:20][CH2:19][CH2:18][N:1]2[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 21958678Ethyl 1-(3-phenylpropyl)pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 4-pyrazole carboxylate (3.57 mmol) in acetone (30 ml) was added potassium carbonate (35.7 mmol) and 1-bromo-3-phenylpropane (3.57 mmol). The suspension was refluxed overnight, after which the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer dried over magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to give an oil, which was purified by preparative TLC, to give ethyl 1-(3-phenylpropyl)pyrazole-4-carboxylate.

Workup

  1. temperatureThe suspension was refluxed overnight
  2. customafter which the solvent was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give an oil, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-57a789f1727f4969851ec17937bcffa5
Source dataset
uspto-grants-2010_06
Patent number
US07741331B2

Linked notes

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