Pyrazole → HCID 64116064, compound

HRID 899263Notes

Reaction equation

HRID 899263 reaction equation
O[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:10]1([CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 24827Acrylic acid, 2-(hydroxymethyl)-, ethyl ester

Product 1

HCID 64116064HCID 64116064, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 2-(hydroxymethyl)acrylate (4.1 g, 32 mmol), pyrazole (2.6 g, 38 mmol) and potassium carbonate (11 g, 79 mmol) in acetonitrile (30 mL) was refluxed for 20 h, quenched by the addition of water (100 mL), and extracted with ethyl acetate (40 mL×2). The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (7/1) to afford 1.0 g (18%) of the title compound as a colorless oil:

Workup

  1. temperaturewas refluxed for 20 h
  2. customquenched by the addition of water (100 mL)
  3. extractionextracted with ethyl acetate (40 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (7/1)

Sources & evidence

ORD record
ord-140aceb104dc48f4808a8eda2e3040f7
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

Loading…