SYNTHESIS OF O-(BETA-HYDROXYETHYL) DERIVATIVES OF DIOSMETIN

Five O-(beta-hydroxyethyl) derivatives (3, 4, 5, 6, 7) of diosmetin ha ve been synthesized for the first time. Compounds 3 and 6 have been ob tained by hydrolysis of 3'-O-(beta-hydroxyethyl)- and 3',5-di-O-(beta- hydroxyethyl)diosmin, respectively. Compound 4 has been prepared from diosmetin, after protecting the hydroxyls at C-7 and C-3', using ethyl ene oxide or ethyl chloroacetate and sodium borohydride, followed by r emoval of the protective groups. Compounds 5 and 7 have been prepared by the reaction of diosmetin (8) and 6 with ethylene chlorohydrin, res pectively.