Pyridine → HCID 86619969, compound

HRID 1712863Notes

Reaction equation

HRID 1712863 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].N1C=CC=CC=1.Cl[C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[C:20]([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:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13041PentafluorophenolHCID 20884Ethoxalyl chloride

Product 1

HCID 86619969HCID 86619969, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 50 ml of toluene, 16.5 g (90 mmol) of pentafluorophenol and 8 ml (99 mmol) of pyridine were dissolved. To the solution, 12.9 g (94 mmol) of ethyl chloroglyoxylate were added dropwise under an ice bath for the reaction. After 1 hour stirring at room temperature, the reaction mixture was filtered and concentrated. The thus obtained crude product was refined by distillation to obtain 13.5 g of pentafluorophenyl ethyl oxalate (colorless liquid). The compound had a melting point of 70 to 71° C./2 mmHg.

Workup

  1. customfor the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customThe thus obtained crude product
  5. distillationwas refined by distillation

Sources & evidence

ORD record
ord-7625779b2ba84494af51b88a129fde8d
Source dataset
uspto-grants-2010_09
Patent number
US07794876B2

Reaction notes

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