Sodium Carbonate → tert-butyl (E)-4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl]piperidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl (E)-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidine-1-carboxylate (0.176 g, 0.501 mmol) in 1,4-dioxane (5 mL) was added with 7-iodo-6-methoxybenzofuran-3(2H)-one (0.145 g, 0.501 mmol) synthesized in Example B46, Step 2, 2 M aqueous sodium carbonate (0.750 mL, 1.50 mmol) and tetrakis(triphenylphosphine)palladium (0.0579 g, 0.0501 mmol), and the mixture was refluxed for 12 hours by heating. The reaction mixture was cooled to room temperature, concentrated, and added with water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (E)-4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)allyl]piperidine-1-carboxylate (0.0313 g, 16%).

Provenance & Evidence