Sodium Iodide → 1-[1-(4-Chlorophenyl)pyrazol-3-yl]oxypropan-2-one

HRID 918758Notes

Reaction equation

HRID 918758 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([OH:13])=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:23][C:24](=[O:26])[CH3:25].[Cl-].[Li+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:23][C:24](=[O:26])[CH3:25])=[N:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 178516414HCID 178516414, compound

Product 1

HCID 896505491-[1-(4-Chlorophenyl)pyrazol-3-yl]oxypropan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.50 g (28.3 mmol) 1-(4-chlorophenyl)pyrazol-3-ol, 3.91 g (28.3 mmol) potassium carbonate and 50 mg sodium iodide in 30 ml DMF have been stirred for 5 min at ambient temperature. Then 2.62 g (28.3 mmol) chloroacetone have been added dropwise while stirring which was continued at 60° C. for 5 h. The mixture was poured into excess 10% aqueous lithium chloride solution and extracted with ethyl acetate three times. The combined extracts have been washed with 10% lithium chloride solution twice and dried with sodium sulfate. After removal of the solvent in vacuo the crude product has been purified by chromatography on silica. Yield 6.5 g. The product was used for the next step.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined extracts have been washed with 10% lithium chloride solution twice
  3. dry with materialdried with sodium sulfate
  4. customAfter removal of the solvent in vacuo the crude product
  5. customhas been purified by chromatography on silica

Sources & evidence

ORD record
ord-e72d08e6ed804b3ab5d961dabde19a3d
Source dataset
uspto-grants-2016_03
Patent number
US09271501B2

Reaction notes

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