Dimethylformamide → methyl 3-methoxy-1-methyl-1H-pyrazole-5-carboxylate

HRID 1667857Notes

Reaction equation

HRID 1667857 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.IC.[C:14](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:14][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178498598HCID 178498598, compound

Product 1

HCID 12226057methyl 3-methoxy-1-methyl-1H-pyrazole-5-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-hydroxy-1-methyl-1H-pyrazole-5-carboxylate (2.34 g, 15.0 mmol), iodomethane (3.19 g, 22.5 mmol), potassium carbonate (4.15 g, 30.0 mmol) and N,N-dimethylformamide (15 mL) was stirred at room temperature for 18 hr. The mixture was diluted with water (50 mL), and extracted with ethyl acetate (50 mL×3). The organic layer was washed with water (10 mL×2), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→50/50) to give the title compound (2.01 g, yield 79%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. washThe organic layer was washed with water (10 mL×2)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→50/50)

Sources & evidence

ORD record
ord-aa243c1f7acf4c1c91df3326b001e450
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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