Ethanol → ethyl(1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetate

HRID 349930Notes

Reaction equation

HRID 349930 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:19][C:20]([OH:22])=[O:21])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:33](O)[CH3:34]>>[CH2:33]([O:21][C:20](=[O:22])[CH2:19][C:11]1[CH:10]=[N:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:34]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 230247242-(1-Benzyl-5-phenyl-1H-pyrazol-4-YL)acetic acid

Product 1

HCID 70122986ethyl(1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetateYield 89%

Procedure

A mixture of (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetic acid (3.70 g), concentrated sulfuric acid (0.5 ml), and ethanol (200 ml) was refluxed for 5 hours. The reaction mixture was alkalinized with saturated aqueous sodium bicarbonate, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl(1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetate (3.62 g, yield: 89%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:6, volume ratio).

Workup

  1. temperaturewas refluxed for 5 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3067b2535a3476796e63ba30364b240
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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