Water → 5-Acetyloxy-1-(4-t-butylphenyl)-3-methyl-1H-pyrazole

HRID 417999Notes

Reaction equation

HRID 417999 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([OH:16])=[CH:14][C:13]([CH3:17])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26].O>O1CCCC1>[C:25]([O:16][C:15]1[N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=2)[N:12]=[C:13]([CH3:17])[CH:14]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178429256HCID 178429256, compound

Product 1

HCID 666507705-Acetyloxy-1-(4-t-butylphenyl)-3-methyl-1H-pyrazoleYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-t-Butylphenyl)-5-hydroxy-3-methyl-1H-pyrazole (21.7 g, 94.1 mmol) in tetrahydrofuran (600 mL) was mixed with triethylamine (26.2 mL, 188 mmol.) and acetyl chloride (7.4 mL, 104 mmol) at 0° C. and stirred at room temperature for 45 minutes. The reaction solution was mixed with water (300 mL), and the aqueous layer and the organic layer were separated. The solvent was removed from the organic layer by distillation, and the residue was mixed with ethyl acetate. The aqueous layer was extracted with ethyl acetate twice, and the extract was combined with the organic layer. The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate once, with water twice and with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give 22.2 g of the desired product (87% yield).

Workup

  1. customthe aqueous layer and the organic layer were separated
  2. customThe solvent was removed from the organic layer by distillation
  3. additionthe residue was mixed with ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate twice
  5. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate once
  6. dry with materialwith water twice and with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cce5b6ef49854f20a4a64213633ae44d
Source dataset
uspto-grants-2012_01
Patent number
US08093251B2

Reaction notes

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