HCID 53760366, compound → HCID 19069252, compound
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.