REACTIONS OF METHYL THREO-2-ACETOXY-3-CHLORO-3-(4-METHOXYPHENYL)PROPANOATE AND METHYL CIS-2,3-EPOXY-3-(4-METHOXYPHENYL)PROPANOATE WITH 3,5-DIMETHOXYPHENOL - POTENTIAL ROUTES TO FLAVAN-3-OLS

Attempted syntheses of flavan-3-ols by reaction of either methyl threo-2-acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate (3) or methyl cis-2,3-epoxy-3-(4-methoxyphenyl)propanoate (14) with 3,5-dimethoxyphenol failed to give the required aryl ethers. Products usually were derived from C-alkylation of the electron-rich phenol although reaction of the chloro acetate (3) with the phenoxide ion gave the furanone (5). The single-crystal X-ray structures of methyl 4-hydroxy-3-(4-methoxyphenyl)-2-(4-methoxyphenylmethyl)-5-oxo-2,5-dihydrofuran-2-carboxylate and cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one have been determined.