I'm attempting an olide synthesis from a paper by B. Sun (Tetrahedron: Asymmetry 16 (2005) 1305-1307).
The procedure, as stated in the article, is:
To a solution of 1mmol of 5a ([hydroxyundecyl]cyclopentanone) in 15mL of anhydrous DCM, 6mmol of NaHCO3, and 6mmol of m-CPBA was added. The reaction mixture is then stirred at rt for 4h, and extracted with Et2O. The organic layer was washed successively wit haq. NaHCO3, water, and brine, and dried. After removal of solvent, the crude product was purified by flash chromatography (2:1 petether/EtOAc). 82% yield.
The obstacle I run into every time is that after work up, my product is
mostly acid!! My colleague has attempted this too, but to no avail.
Does anyone see any problem with the prep? Or does anyone know a better solution?