Glyoxal → HCID 56949783, compound

HRID 1880346Notes

Reaction equation

HRID 1880346 reaction equation
[CH:1]([CH:3]=O)=[O:2].[CH:5]1([NH:9][N:10]=[CH:11][C:12](=[O:14])[CH3:13])[CH2:8][CH2:7][CH2:6]1>O>[OH:14][C:12]1[C:11]([C:1](=[O:2])[CH3:3])=[N:10][N:9]([CH:5]2[CH2:8][CH2:7][CH2:6]2)[CH:13]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 66920544HCID 66920544, compound

Product 1

HCID 56949783HCID 56949783, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 40% aqueous solution of glyoxal (1.13 mL, 9.84 mmol) was added to 2-oxopropanal cyclobutylhydrazone (1.38 g, 9.84 mmol) in H2O (70 mL). The mixture was then heated at reflux. After 1 hour, the mixture was cooled to room temperature and extracted with CH2Cl2 (4×). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford 1.53 g (86%) of 1-(4-hydroxy-1-cyclobutyl-1H-pyrazol-3-yl)ethanone as a yellow oil. The crude product was then used in the next step without further purification.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux
  3. extractionextracted with CH2Cl2 (4×)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88e2df09657349a7943ef883dc254e58
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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