Methanol → methyl 1-(3-chloro-2-pyridinyl)-3-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]-1H-pyrazole-5-carboxylate

HRID 2427125Notes

Reaction equation

HRID 2427125 reaction equation
[F:1][C:2]([O:6][C:7]([F:10])([F:9])[F:8])=[C:3]([F:5])[F:4].[Cl:11][C:12]1[C:13]([N:18]2[C:22]([C:23]([O:25][CH2:26]C)=[O:24])=[CH:21][C:20]([OH:28])=[N:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1.[OH-].[K+].CO>O.CS(C)=O>[Cl:11][C:12]1[C:13]([N:18]2[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]([O:28][C:3]([F:5])([F:4])[CH:2]([F:1])[O:6][C:7]([F:10])([F:9])[F:8])=[N:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14474Perfluoro(methyl vinyl ether)HCID 14797Potassium HydroxideHCID 178469376HCID 178469376, compound

Product 1

HCID 86632567methyl 1-(3-chloro-2-pyridinyl)-3-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Trifluoromethyl trifluorovinyl ether was blown into a mixture of 1.0 g of ethyl 1-(3-chloro-2-pyridinyl)-3-hydroxy-1H-pyrazole-5-carboxylate, 0.042 g of potassium hydroxide, 10 ml of methanol and 10 ml of dimethyl sulfoxide under ice-cooling. The resulting mixture was stirred at room temperature for 4 days. Water was poured into the reaction mixture, and the mixture was extracted with diethyl ether two times. The organic layers were combined, washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 1.32 g of methyl 1-(3-chloro-2-pyridinyl)-3-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]-1H-pyrazole-5-carboxylate of the formula:

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with diethyl ether two times
  3. washwashed with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76592361c6f44edab457e61ea133ce26
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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