Citric Acid → Tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate

Participants

Reaction Conditions

Reaction Steps

Phenol (0.029 mL), cesium carbonate (0.11 g), 2,2,6,6-tetramethylheptane-3,5-dione (3.4 μL), and copper(I) chloride (8.2 mg) were added to a 1-methyl-2-pyrrolidone (0.60 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-iodobenzamido)-4-phenylbenzoate (0.10 g), followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, and then 2,2,6,6-tetramethylheptane-3,5-dione (3.4 μL) and copper(I) chloride (8.2 mg) were added thereto, followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. 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 [eluent: 100-95% hexane/ethyl acetate] to obtain 0.049 g of tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate (0.049 g).

Provenance & Evidence