Réaction #792181

ord-371274c08704439eae6a0827d3fcb3cb

Équation de réaction

[K+].[OH-]
Potassium hydroxide
CCOC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate
CCOC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
product
CCOC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate
O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
product
Rendement 93.0%
O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid
Rendement 93.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe solvent was removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe mixture was dissolved in water (40 mL)
  3. 3
    LavageThe solution was washed with ethyl acetate (20 mL)
  4. 4
    Extractionwas extracted with ethyl acetate (3×20 mL)
  5. 5
    AutreThe combined extracts were dried
  6. 6
    Autreevaporated
  7. 7
    Autreto give

Mode opératoire

Potassium hydroxide (0.5 g, 85%, 2.28 mmol) in water (1 mL) was added to ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (i.e. the product of Step D) (0.66 g, 2.07 mmol) in ethanol (3 mL). After about 30 minutes, the solvent was removed under reduced pressure, and the mixture was dissolved in water (40 mL). The solution was washed with ethyl acetate (20 mL). The aqueous layer was acidified with concentrated hydrochloric acid and was extracted with ethyl acetate (3×20 mL). The combined extracts were dried and evaporated to give the product as a solid (0.53 g, 93% yield), m.p. 178-179° C. (after crystallization from hexanes-ethyl acetate).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09173400B2uspto-grants-2015_11