Water → HCID 17862887, compound

HRID 1172111Notes

Reaction equation

HRID 1172111 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[NH:10]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[N:11]1.O>CN(C)C=O>[CH2:7]([N:10]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[N:11]1)[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 17862887HCID 17862887, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.7 g (26.8 mmoles) of anhydrous potassium carbonate and 4.2 g (26.6 mmoles) of ethyl iodide were added to a solution of 1.5 g (10.7 mmoles) of ethyl 1H-pyrazole-4-carboxylate dissolved in 50 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 20 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 1.6 g (yield: 88.9%) of ethyl 1-ethyl-1H-pyrazole-4-carboxylate as a yellow oily substance.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter confirmation of the completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Sources & evidence

ORD record
ord-8dd2a20c9bd846979a19f42cce7dd01c
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

Loading…