Pyridinium → HCID 19069252, compound

HRID 1957334Notes

Reaction equation

HRID 1957334 reaction equation
[CH:1]1([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([CH:12]=[O:13])=[CH:14][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4989215PyridiniumHCID 53760366HCID 53760366, compound

Product 1

HCID 19069252HCID 19069252, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol prepared above (4.24 g, 20.7 mmol) was dissolved in 250 mL methylene chloride under an atmosphere of dry nitrogen. Pyridinium chlorochormate (5.62 g, 26.1 mmol) was added over 5 minutes. After stirring at ambient temperature for 72 hours, the mixture was filtered through Celite and concentrated in vacuo. Flash silica gel chromatography eluting with 10% ethyl acetate in hexane afforded 3.25 g (77%) of the title compound.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. washFlash silica gel chromatography eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8fd926940899474bbd0f19a5fede7ff9
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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