Water → HCID 58542532, compound

HRID 1843082Notes

Reaction equation

HRID 1843082 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1.[Na+].Cl[C:14]([F:19])([F:18])C([O-])=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:10][O:9][C:7]([C:5]1[N:4]([CH3:11])[N:3]=[C:2]([O:1][CH:14]([F:19])[F:18])[CH:6]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 178498598HCID 178498598, compound

Product 1

HCID 58542532HCID 58542532, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2.00 g (12.8 mmol) of methyl 3-hydroxy-1-methyl-1H-pyrazole-5-carboxylate (preparation: Chem. Ber. 1974, 107, 1318-1328) in 28 ml of N,N-dimethylformamide is admixed with 5.09 g (32.0 mmol, 96%) of chlorodifluoroacetic acid sodium salt and 2.66 g (19.2 mmol) of potassium carbonate, and the reaction mixture is heated at 80° C. overnight. The reaction mixture is added to 300 ml of water and extracted several times with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated by evaporation in vacuo on a rotary evaporator. Chromatographic purification gives 1.07 g of methyl-3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate (40%).

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation in vacuo on a rotary evaporator
  5. customChromatographic purification

Sources & evidence

ORD record
ord-7097c840edfe402290cef8687ab25305
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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