Glyoxal → 95884-20-1

HRID 1880334Notes

Reaction equation

HRID 1880334 reaction equation
[CH:1]([CH:3]=O)=[O:2].[CH3:5][NH:6][N:7]=[CH:8][C:9](=[O:11])[CH3:10]>O>[OH:11][C:9]1[C:8]([C:1](=[O:2])[CH3:3])=[N:7][N:6]([CH3:5])[CH:10]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 727702682-Oxopropanal methylhydrazone

Product 1

HCID 1341338895884-20-1Yield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 40% aqueous solution of glyoxal (7.1 mL, 62 mmol) was added a solution of 2-oxopropanal methylhydrazone (6.17 g, 61.6 mmol) in water (300 mL). The mixture was heated at reflux for 1 hour before cooling to room temperature. The mixture was extracted with CH2Cl2 (4×). The combined organic extracts were dried over NaSO4, filtered, concentrated and purified by CombiFlash (120 g column, 30-40% EtOAc/hexanes gradient) to provide 1-(4-hydroxy-1-methyl-1H-pyrazol-3-yl)ethanone (5.93 g, 69%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. extractionThe mixture was extracted with CH2Cl2 (4×)
  4. dry with materialThe combined organic extracts were dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by CombiFlash (120 g column, 30-40% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-1eb41b0f354b495eb2d12d0b59540f98
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

Loading…