Glyoxal → HCID 66920583, compound

HRID 1880345Notes

Reaction equation

HRID 1880345 reaction equation
[CH:1]([CH:3]=O)=[O:2].[CH:5]1([NH:10][N:11]=[CH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:8][CH2:7][CH2:6]1>O>[OH:15][C:13]1[C:12]([C:1](=[O:2])[CH3:3])=[N:11][N:10]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9]2)[CH:14]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 66920356HCID 66920356, compound

Product 1

HCID 66920583HCID 66920583, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 40% aqueous solution of glyoxal (1.88 mL, 16.4 mmol) was added to 2-oxopropanal cyclopentylhydrazone (2.53 g, 16.4 mmol) in H2O (125 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 1.68 g (53%) of 1-(4-hydroxy-1-cyclopentyl-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-6c50b52bce77403c905619205cfbf87a
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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