Ethanol → Ethyl 1-ethyl-1H-pyrazole-5-carboxylate

HRID 244659

Reaction equation

HRID 244659 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[N:4]1)[CH3:2].S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH2:16][CH3:17])=[O:9])=[CH:6][CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5657021-Ethyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 23005846Ethyl 1-ethyl-1H-pyrazole-5-carboxylate

Procedure

To a solution of 1-ethyl-1H-pyrazole-5-carboxylic acid (950 mg) (for example, available from Fluorochem) in ethanol (50 ml) was added sulphuric acid (0.5 ml) and the mixture stirred at reflux under nitrogen for 70 h. The solvent was removed in vacuo and the residue partitioned between DCM (25 ml) and saturated sodium bicarbonate solution (25 ml) and separated using a hydrophobic frit. The aqueous layer was washed with DCM (2×20 ml) and the organic phases were combined. The solvent was removed in vacuo to give the title compound (1.09 g) as a colourless oil.

Workup

  1. temperatureat reflux under nitrogen for 70 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between DCM (25 ml) and saturated sodium bicarbonate solution (25 ml)
  4. customseparated
  5. washThe aqueous layer was washed with DCM (2×20 ml)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d52b561c3c0e42b09f4229878d584849
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Linked notes

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