Hydrochloric Acid → 5-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dione

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Reaction Steps

10.07 g of 5-[4-(2,2-diethoxyethoxy)benzyl]-thiazolidine-2,4-dione (prepared as described in Preparation 19) were dissolved in 80 ml of tetrahydrofuran, and then 20 ml of 6N aqueous hydrochloric acid were added to the resulting solution. The mixture was then left to stand at room temperature overnight. At the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the resulting residue, which was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extract by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 3:2 by volume mixture of ethyl acetate and hexane as the eluent, to give 5.92 g of the title compound having an Rf value of 0.37 (on silica gel thin layer chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Provenance & Evidence