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

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Reaction Steps

A solution of tert-butyl (E)-4-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl]piperidine-1-carboxylate (0.253 g, 0.750 mmol) in 1,4-dioxane (5 mL) was added with 7-iodo-6-methoxybenzofuran-3(2H)-one (0.198 g, 0.682 mmol) synthesized in Example B46, Step 2, 2 M aqueous sodium carbonate (0.680 mL, 1.36 mmol) and tetrakis(triphenylphosphine)palladium (0.0788 g, 0.0682 mmol), and the mixture was refluxed for 10 hours by heating. The reaction mixture was cooled to room temperature, and then added with water, and 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 subjected to silica gel column chromatography (chloroform/methanol), and the resulting crude product was further purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (E)-4-[2-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)vinyl]piperidine-1-carboxylate (0.0692 g, 27%).

Provenance & Evidence