Dimethyl Sulfoxide → Mitoglitazone

Participants

Reaction Steps

A mixture of 5-[4-[2-(5-ethyl-2-pyridyl)-2-hydroxyethoxy]benzyl]-2,4-thiazolidinedione. 1/2 C2H5OH (396 mg), acetic anhydride (1.5 ml) and dimethylsulfoxide (4 ml) was stirred at room temperature for 5 hours and then poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate and the solvent was distilled off. The oily residue was subjected to silica gel chromatography. A fraction eluted with chloroform-methanol (100:1, v/v) gave 5-[4-[2-(5-ethyl-2-pyridyl)-2-oxoethoxy]benzyl]-2,4-thiazolidinedione (75 mg, yield: 20%). This was recrystallized from ethyl acetate-hexane to obtain colorless prisms, m.p. 148°-149° C.

Provenance & Evidence