Reaction #1909810

Reaction equation

water

1-(1-methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole

1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole

sodium hydride

→

2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile

Yield 57.5%

Solvents

THF

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas dropwise added
2. 2
   workup.STIRRINGat 50° C. and then stirred overnight at room temperature
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Washwashed with a small amount of water
5. 5
   DryingThe resulting product was dried over sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   OtherThe residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1

Procedure

A solution of 0.5 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole dissolved in 10 ml of THF was dropwise added to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF, at 50° C. After the resulting product was stirred for 30 minutes, a solution of 0.67 g of 1-(1-methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole dissolved in 10 ml of THF was dropwise added thereto at 50° C. and then stirred overnight at room temperature. The reaction mixture was poured into water, then extracted with ethyl acetate and washed with a small amount of water. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1 to obtain 0.52 g of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile.

Source