HCID 53760366, compound → HCID 19069252, compound

HRID 1781144Notes

Reaction equation

HRID 1781144 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.[Cr](Cl)([O-])(=O)=O.[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 53760366HCID 53760366, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19069252HCID 19069252, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol resulting from Example 37A (4.24 g, 20.7 mmol) was dissolved in 250 mL of methylene chloride under an atmosphere of dry nitrogen. Pyridinium chlorochromate (5.62 g, 26.1 mmol) was added over 5 minutes. After stirring at ambient temperature 72 hours, the mixture was filtered through Celite® and concentrated in vacuo. Flash chromatography on silica gel 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

Sources & evidence

ORD record
ord-12c32416dd51410dbbe39f4fd84d7649
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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