Thiazolidinedione → HCID 16392506, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-thiazolidine-2,4-dione (10 g, 85.38 mmol, 1.00 equiv) in tetrahydrofuran (300 mL), 2-bromoethan-1-ol (10.6 g, 84.82 mmol, 1.00 equiv), triphenylphosphane (27 g, 102.94 mmol, 1.20 equiv). This was followed by the addition of a solution of DIAD (21 g, 103.96 mmol, 1.20 equiv) in tetrahydrofuran (30 mL) dropwise with stirring at 0-10° C. in 30 min. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/50) to give 9 g (47%) of 3-(2-bromoethyl)-1,3-thiazolidine-2,4-dione as a colorless oil.

Provenance & Evidence