Thiazolidinedione → 5-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl)-propyl}-2-methyl-benzylidene)-thiazolidine-2,4-dione

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Reaction Steps

To a mixture of enantiomer 1 of 4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde (0.64 g, 1.61 mmol) and toluene (20 mL) is added 90% 2,4-thiazolidinedione (0.25 g, 1.94 mmol), and piperidine acetate (0.04 g, 0.24 mmol). The solution is heated to a reflux overnight and the water removed by a Dean-Stark trap. The solution is diluted with EtOAc (60 mL), washed with water (50 mL), saturated NaHCO3 (50 mL), dried over MgSO4, filtered and concentrated. Purified by ISCO (20%-50% EtOAc gradient) to furnish the title compound (0.75 g, 1.51 mmol, 94%).

Provenance & Evidence