Pyridinium → 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.[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 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.