Citric Acid → Benzyl 2-(benzyloxy)-4-(pyridin-3-yl)benzoate

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Reaction Steps

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine (0.24 g), tripotassium phosphate (0.46 g), palladium(II) acetate (4.5 mg) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (4.1 mg) were added to a toluene (5.3 mL) solution of benzyl 2-(benzyloxy)-4-chlorobenzoate (0.35 g), followed by heating to reflux under a nitrogen atmosphere for 3 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.16 g), tripotassium phosphate (0.25 g), palladium(II) acetate (4.5 mg), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (4.1 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 3 hours and 30 minutes. After cooling the reaction mixture to room temperature, a 10% aqueous solution of citric acid and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-50% hexane/ethyl acetate] to obtain 0.35 g of benzyl 2-(benzyloxy)-4-(pyridin-3-yl)benzoate.

Provenance & Evidence