Pyruvic Acid → HCID 20084657, compound

HRID 1609399Notes

Reaction equation

HRID 1609399 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].C1(N=C=NC2CCCCC2)CCCCC1.[C:28](O)(=[O:32])[C:29]([CH3:31])=[O:30]>ClCCl>[C:28]([O:8][C:7]1[C:2]([F:1])=[C:3]([F:12])[C:4]([F:11])=[C:5]([F:10])[C:6]=1[F:9])(=[O:32])[C:29]([CH3:31])=[O:30]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 20084657HCID 20084657, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

736 mg (4 mmol) of pentafluorophenol and 825 mg (4 mmol) of dicyclohexylcarbodiimide were added to a stirred solution of 352 mg (4 mmol) of pyruvic acid in 10 ml of dichloromethane at 0° C. under nitrogen. The mixture obtained was diluted with 40 ml of dichloromethane and stirred at room temperature for 18 hours. The solvent was removed under reduced pressure. The residue was treated with 5 ml of cold ethyl acetate. The mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by flash chroma- tography on silica gel using ethyl acetate/dichloromethane (1:8) for the elution to give 802 mg of pentafluorophenyl pyruvate.

Workup

  1. customThe mixture obtained
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was treated with 5 ml of cold ethyl acetate
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was purified by flash chroma- tography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-bb7036019f0342ab8bdb93cfce6f00d5
Source dataset
uspto-grants-1995_03
Patent number
US05399712

Reaction notes

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