Water → 1-tert-butyl-5-methoxy-3-trifluoromethyl-1H-pyrazole

HRID 1292797Notes

Reaction equation

HRID 1292797 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[C:9]([N:13]1[C:17](O)=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[N:14]1)([CH3:12])([CH3:11])[CH3:10].O>CN(C)C=O>[C:9]([N:13]1[C:17]([O:4][CH3:1])=[CH:16][C:15]([C:19]([F:21])([F:22])[F:20])=[N:14]1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178448751HCID 178448751, compound

Product 1

HCID 178629171-tert-butyl-5-methoxy-3-trifluoromethyl-1H-pyrazoleYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.0 g (108.4 mmoles) of anhydrous potassium carbonate and 19.3 g (135.5 mmoles) of methyl iodide were added, at room temperature, to a solution of 18.8 g (90.3 mmoles) of 1-tert-butyl-3-trifluoromethyl-1H-pyrazol-5-ol dissolved in 100 ml of N,N-dimethylformamide. The mixture was stirred for 15 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with diethyl ether. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 20.0 g (yield: 99.8%) of 1-tert-butyl-5-methoxy-3-trifluoromethyl-1H-pyrazole.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction with diethyl ether
  5. washThe resulting organic layer was washed with water
  6. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent

Sources & evidence

ORD record
ord-4c6cfb683dc84eb7891f056275e4fdc9
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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