Water → 1-Allyl-1H-pyrazole-5-carbaldehyde

HRID 31544

Reaction equation

HRID 31544 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](Br)[CH:15]=[CH2:16].O>CN(C=O)C>[CH2:16]([N:2]1[C:3]([CH:6]=[O:7])=[CH:4][CH:5]=[N:1]1)[CH:15]=[CH2:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 122183831H-Pyrazole-3-carbaldehyde

Product 1

HCID 235104011-Allyl-1H-pyrazole-5-carbaldehydeYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrazole-3-carbaldehyde (3.00 g, 31.2 mmol) was dissolved in DMF (20 ml), and thereto were added potassium carbonate (6.47 g, 46.8 mmol) and allyl bromide (3.50 g, 32.8 mmol) with stirring. The mixture was stirred at room temperature for 6 hours, and thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (429 mg, 10%).

Workup

  1. stirringThe mixture was stirred at room temperature for 6 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fbfff4f61fb142d68d6b767e74c32fa3
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Linked notes

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