Water → HCID 178466979, compound

HRID 418000Notes

Reaction equation

HRID 418000 reaction equation
C([O:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][CH:11]=2)[N:8]=[C:7]([CH3:20])[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O.[O:28]1CCO[CH2:30][CH2:29]1>>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([N:9]2[C:5]([OH:4])=[C:6]([C:29](=[O:28])[CH3:30])[C:7]([CH3:20])=[N:8]2)=[CH:15][CH:14]=1)([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 666507705-Acetyloxy-1-(4-t-butylphenyl)-3-methyl-1H-pyrazole

Product 1

HCID 178466979HCID 178466979, compoundYield 66%

Procedure

5-Acetyloxy-1-(4-t-butylphenyl)-3-methyl-1H-pyrazole (4.21 g, 15.5 mmol) in 1,4-dioxane (150 mL) was stirred with potassium carbonate (2.14 g, 15.5 mmol) at 110° C. for 3.5 hours, and after addition of water (50 mL), the organic solvent was removed by distillation. Then, ethyl acetate, water and 6 M hydrochloric acid were added to adjust the aqueous layer to pH 2, and the aqueous layer and the organic layer were separated. The aqueous layer was extracted with ethyl acetate twice, and the organic layer was combined with the extract, washed with saturated aqueous ammonium chloride three times and with saturated aqueous sodium chloride once and dried over anhydrous sodium sulfate and filtered. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1→3/1→1/1) to give 2.77 g of the desired product (66% yield).

Workup

  1. customthe organic solvent was removed by distillation
  2. additionThen, ethyl acetate, water and 6 M hydrochloric acid were added
  3. customthe aqueous layer and the organic layer were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate twice
  5. washwashed with saturated aqueous ammonium chloride three times and with saturated aqueous sodium chloride once
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed by distillation
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1→3/1→1/1)

Sources & evidence

ORD record
ord-c0e30454777441b6b4d98fad3b9e9201
Source dataset
uspto-grants-2012_01
Patent number
US08093251B2

Reaction notes

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