HCID 19360783, compound → HCID 19360787, compound

Participants

Reaction Steps

Sodium periodate (14.2 g) was dissolved in water (175 ml) and ruthenium trichloride (0.7 g) added to give a black solution. The solution was stirred during the addition of 3-(3-bromo-4-chlorophenyl)-5-hydroxythiazolidin-4-one (7.85 g) in methanol (35 ml) over 5 min, the reaction vessel was cooled in an ice bath to control the resulting exotherm. The mixture was stirred for 1 hour before quenching with sodium metabisulfite. The mixture was extracted with ethyl acetate and the combined organic extracts washed with aqueous sodium metabisulfite solution and water, then dried (MgSO4). Evaporation of the solvent under reduced pressure gave a gum which was triturated with dichloromethane to give the title compound as a grey solid (1.13 g), m.p. 139-140° C.

Provenance & Evidence