Water → 926913-59-9

HRID 1952257Notes

Reaction equation

HRID 1952257 reaction equation
I[C:2]1[C:3]([CH3:12])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].C([Li])CCC.[OH2:18].[O:19]1[CH2:23]CCC1>CCCCCC.C(=O)=O>[CH3:11][N:5]1[C:6]([C:7]([F:10])([F:9])[F:8])=[C:2]([C:23]([OH:19])=[O:18])[C:3]([CH3:12])=[N:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 60136710HCID 60136710, compoundHCID 178418339Butyllithium

Product 1

HCID 68954028926913-59-9Yield 74%

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

4-Iodo-1,3-dimethyl-5-trifluoromethylpyrazole (8.7 g, 30 mmol) was dissolved in tetrahydrofuran (87 ml), and a solution (1.6 M, 28 ml) of n-butyl lithium in hexane was slowly added under an argon atmosphere with cooling with dryice-acetone (not higher than −60° C.). After stirring at −70° C. for 30 min, the mixture was gradually warmed to room temperature while blowing in carbon dioxide. The reaction mixture was poured into water, the organic layer was removed, and the aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained crude crystals were washed with hexane to give the desired compound (4.67 g) as crystals.

Workup

  1. temperaturethe mixture was gradually warmed to room temperature
  2. customthe organic layer was removed
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude crystals
  8. washwere washed with hexane

Sources & evidence

ORD record
ord-beb389f1524247e597fa598a668d66ce
Source dataset
uspto-grants-2013_03
Patent number
US08404861B2

Reaction notes

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