Ethanol → 1-tert-butyl-3-(trifluoromethyl)-1H-pyrazole

HRID 2427048Notes

Reaction equation

HRID 2427048 reaction equation
C(O[CH:4]=[CH:5][C:6](=O)[C:7]([F:10])([F:9])[F:8])C.C([O-])(=O)C.[Na+].C(O)C.Cl.[C:21]([NH:25][NH2:26])([CH3:24])([CH3:23])[CH3:22]>O>[C:21]([N:25]1[CH:4]=[CH:5][C:6]([C:7]([F:8])([F:9])[F:10])=[N:26]1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 81889tert-Butylhydrazine monohydrochlorideHCID 517045Sodium AcetateHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-one

Product 1

HCID 233959871-tert-butyl-3-(trifluoromethyl)-1H-pyrazoleYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5 g of 4-ethoxy-1,1,1-trifluoro-3-butene-2-one, 3 g of sodium acetate and 15 ml of ethanol was added 4.6 g of tert-butylhydrazine hydrochloride, and the mixture was heated to reflux for 2 days. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3.0 g of 1-tert-butyl-3-trifluoromethyl-1H-pyrazole of the formula:

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 days
  3. extractionthe mixture was extracted with diethyl ether three times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03cc02a24a004e5eb9c09081ebe14e61
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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