تفاعل #792181

ord-371274c08704439eae6a0827d3fcb3cb

معادلة التفاعل

[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
المردود 93.0%
O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid
المردود 93.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe solvent was removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe mixture was dissolved in water (40 mL)
  3. 3
    غسيلThe solution was washed with ethyl acetate (20 mL)
  4. 4
    استخلاصwas extracted with ethyl acetate (3×20 mL)
  5. 5
    أخرىThe combined extracts were dried
  6. 6
    أخرىevaporated
  7. 7
    أخرىto give

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09173400B2uspto-grants-2015_11