反应详情

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.

1. temperatureby heating
2. temperatureto reflux under a nitrogen atmosphere for 3 hours and 30 minutes
3. temperatureby heating
4. temperatureto reflux under a nitrogen atmosphere for 3 hours and 30 minutes
5. temperatureAfter cooling the reaction mixture to room temperature
6. customthe insoluble substance was removed by filtration
7. customThe organic layer was separated
8. washwashed with a saturated aqueous solution of sodium chloride
9. dry with materialdried over anhydrous magnesium sulfate
10. customthe solvent was evaporated under reduced pressure
11. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-50% hexane/ethyl acetate]