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Abstract: An efficient, simple and economic Morita‐Baylis‐Hillman approach for construction of 3‐hydroxy‐3‐substituted‐2‐oxindole was proceeded smoothly from isatin derivatives and methyl acrylate/acrylonitrile using mild catalytic conditions. It was demonstrated that proper selection of catalyst and reaction medium would differentiate the feasibility of reaction and yield of the final product. Reaction condition was explored the novel combination of Copper Iodide (CuI) and 1,8‐Diazabicyclo [5.4.0] undec‐7‐ene (DBU) in the presence of dichloromethane (DCM) as the medium. This strategy provides a facile access to various derivatives with good to excellent yields in short span of time. The resulting derivatives can serve as a valuable synthetic building block for pharmaceuticals and natural products.