Dimethylformamide → ethyl 5-isobutoxy-1-(2-methylphenyl)-1H-pyrazole-3-carboxylate

HRID 507938Notes

Reaction equation

HRID 507938 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:5]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:30](Br)[CH:31]([CH3:33])[CH3:32]>C(OCC)(=O)C>[CH2:30]([O:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:5]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=1)[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 178469351HCID 178469351, compound

Product 1

HCID 23157226ethyl 5-isobutoxy-1-(2-methylphenyl)-1H-pyrazole-3-carboxylateYield 87.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 5-hydroxy-1-(2-methylphenyl)-1H-pyrazole-3-carboxylate (1.0 g, 4.06 mmol), potassium carbonate (0.84 g, 6.09 mmol) and N,N-dimethylformamide (10 mL) was added isobutyl bromide (0.49 mL, 4.47 mmol) under stirring at room temperature, and the mixture was stirred at the same temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and 5% aqueous potassium hydrogensulfate solution, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (1.07 g, yield 87%) as pale-yellow crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 16 hr
  2. washwashed with water and 5% aqueous potassium hydrogensulfate solution
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

Sources & evidence

ORD record
ord-7270bdbe4797467e9fe56a173eae0be5
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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