Methyl iodide → ethyl 3-acetyl-1-methyl-1H-pyrazole-5-carboxylate

HRID 715920Notes

Reaction equation

HRID 715920 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]([CH3:14])[N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 162204305-Acetyl-2H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 71306158ethyl 3-acetyl-1-methyl-1H-pyrazole-5-carboxylateYield 65.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-acetyl-1H-pyrazole-5-carboxylate (Chem. Commun., 2004, 394-395) (4.82 g) was dissolved in N,N-dimethylformamide (80 ml). To the solution, potassium carbonate (4.39 g) and iodomethane (1.98 ml) were added under ice cooling, and the mixture was stirred at room temperature for 3 hours and 50 minutes. The reaction solution was diluted with ethyl acetate. The organic layer was washed with saturated saline, water, and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (3.38 g).

Workup

  1. washThe organic layer was washed with saturated saline, water, and saturated saline in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-aa9be722dc794806b221efba7b5e5bd4
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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