A series of some new aryl propionic acid derivatives as 2‐(6‐(substituted phenylethynyl)‐2,3‐dihydrobenzofuran‐3‐yl)acetic acids were synthesized. The targeted molecules were prepared by using techniques such as efficient and high‐performance autoclave hydrogenation to reduce highly stable π‐electron system of furan ring and microwave‐assisted rapid Sonogashira Cross‐Coupling reaction between aryl triflate derivatives and substituted aryl acetylenes. The anti‐diabetic screening of selected compounds was performed by using alloxan‐induced diabetic model. The studies include acute and chronic toxicity, effectiveness, change in the behavioral pattern and change in glucose level of the tested animals. The compound 2‐(6‐((4‐ethylphenyl)ethynyl)‐2,3‐dihydrobenzofuran‐3‐yl)acetic acid exhibited maximum anti‐hyperglycemic properties. All the synthesized compounds were characterized by spectroscopic techniques such as 1H‐NMR, 13C‐NMR, IR, Mass spectrometry and single crystal XRD (MTS‐201).