Iodoethane → Ethyl 1-ethyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 374420Notes

Reaction equation

HRID 374420 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][NH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH3:22].C(OCC)(=O)C>C(#N)C.O>[CH2:11]([O:10][C:8]([C:7]1[C:3]([C:2]([F:1])([F:13])[F:14])=[N:4][N:5]([CH2:21][CH3:22])[CH:6]=1)=[O:9])[CH3:12]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178469923HCID 178469923, compound

Product 1

HCID 18996914Ethyl 1-ethyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Ethyl 3-trifluoromethylpyrazole-4-carboxylate (5 g), potassium carbonate (3.48 g) and ethyl iodide (2.3 ml) in acetonitrile were heated at reflux overnight. After cooling, ethyl acetate and water were added and the organic phase separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried (magnesium sulphate) and evaporated under reduced pressure to give a yellow oil which was purified by crystallisation in hexane to produce 4-ethoxycarbonyl-1-ethyl-3-trifluoromethylpyrazole as white crystals (3.65 g), 1H NMR (CDCl3) δ1.25(3H,t), 1.45(3H,t), 4.10(2H,q), 4.20(2H,q) 7.90(1H,s) ppm.

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. customthe organic phase separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  6. customevaporated under reduced pressure
  7. customto give a yellow oil which
  8. customwas purified by crystallisation in hexane

Sources & evidence

ORD record
ord-cb7a01555c604140a97f58ce6354160e
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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