To a solution of ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate (1.2 g, 4.16 mmol) in 10 ml anhydrous dioxane was added potassium phosphate (1.32 g, 6.2 mmol), 3-cyanophenyl boronic acid (0.612 g, 4.16 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 50 ml ethyl acetate, washed with 2×50 ml water, 2×50 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (0.7 g, 71%) as a light yellow oil after drying. ES-MS (M+H+): 242.15. H1NMR (CDCl3) δ: 1.09-1.13 (t, 3H); 1.96-2.01 (m, 2H); 2.80-2.84 (m, 4H); 7.39-7.59 (m, 4H).
