Palladium(II) acetate (0.05 equiv.) was added to a solution of n-butyl acrylate (0.27 mL, 1.5 mmol, 0.50 equiv.), 1-(triisopropylsilyl)-1H-pyrrole (1.34 g, 3.00 mmol), and tert-butyl peroxybenzoate (0.56 mL, 1.5 mmol, 0.50 equiv.), in acetic acid/dioxane/dimethylsulfoxide (0.23/0.69/0.08 mL). The mixture was stirred at 35° C. for 24 h, diluted with diethyl ether (200 mL) and water (20 mL), and filtered through a plug of celite. The organic phase was separated and washed with saturated NaHCO3 solution (2×30 mL) and water (30 mL). The combined aqueous layers were further extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by CC (SiO2, EtOAc/petroleum ether 1:20) to give (E)-butyl 3-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]acrylate (0.70 g, 67%) as a light-yellow oil.
