4-Ethoxy-1,1,1-trifluoro-3-buten-2-one → 3-(Trifluoromethyl)pyrazole

HRID 1675425Notes

Reaction equation

HRID 1675425 reaction equation
[Cl-].[NH2:2][NH2:3].C(O[CH:7]=[CH:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])C>CCO>[F:11][C:10]([F:13])([F:12])[C:9]1[CH:8]=[CH:7][NH:3][N:2]=1

Participants

4

Reactant 2

HCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-oneHCID 21958405HCID 21958405, compound

Product 1

HCID 18070343-(Trifluoromethyl)pyrazoleYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of hydrazine monochloride (6.62 g, 1.6 eq.) in EtOH (300 mL) was added dropwise compound 84 (10.16 g, 1 eq.) in EtOH (200 mL). The reaction mixture was refluxed for 6 hrs and evaporated to dryness. Water and EtOAc were added to the residue. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 86a as a brown solid in 86% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hrs
  2. customevaporated to dryness
  3. additionWater and EtOAc were added to the residue
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-034f3beda66c44bdb71c04426fc67cad
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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