Sodium Carbonate → Ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-hydroxycyclopentan-1-yl}methyl]phenoxy]acetate

Participants

Reaction Steps

To a solution of a mixture (300 mg) of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl}methyl]phenoxy]acetate and ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl}methyl]phenoxy]acetate in methylene chloride (10 ml) were added sodium carbonate (100 mg) and m-chloroperbenzoic acid (200 mg) at 0° C. After being stirred for 2 hours, the reaction mixture was washed with water and brine and dried over magnesium sulfate. After the solvent was evaporated, the residue containing a mixture of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1,2-epoxycyclopentan-1-yl}methyl]phenoxy]acetate and ethyl [3-[(2-(4,5-diphenyloxazol-2-yl)-2,3-epoxycyclopentan-1-yl]methyl]phenoxy]acetate was dissolved in a mixture of ethyl acetate-ethanol (20 ml-10 ml), and thereto was added 10% palladium on carbon (50 mg). After being stirred for 6 hours under hydrogen atmosphere, the reaction mixture was filtered. The solvent was evaporated in vacuo, the residue was chromatographed on silica gel. The first fraction gave ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-hydroxycyclopentan-1-yl}methyl]phenoxy]acetate (70 mg).

Provenance & Evidence