Present communication describes the attempts made to improve the yields of thiazolidinedione group of derivatives keeping in view of their anti-cancer activity. 5-benzylidine-1,3-thiazolidine-2,4-dione derivatives were the active substrates belonging to α-glucosidase inhibitor classification. These were prepared by the reaction of 4-((Z)-(2,4-dioxothiazolidin-5-ylidene) methyl) benzaldehyde with aromatic/hetero aromatic ketones in the presence of potassium hydroxide and ethanol as solvent. Synthesis of 5-benzylidine-1, 3-thiazolidine-2,4-dione derivatives has been optimized under solvent free condition by screening with different bases in order to achieve the required target (of improving the yields). The solvent free condition has resulted in excellent improvement in yields and reduced the manufacturing cost significantly.