反应详情

Piperidine (1.1 mL), cesium carbonate (4.9 g), tris(dibenzylideneacetone)dipalladium(0) (0.069 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.18 g), and palladium(II) acetate (0.034 g) were added to a toluene (30 mL) solution of benzyl 2-(benzyloxy)-5-bromobenzoate (3.0 g), followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and then piperidine (0.37 mL), cesium carbonate (1.2 g), tris(dibenzylideneacetone)dipalladium(0) (0.069 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.18 g), and palladium(II) acetate (0.034 g) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 5 hours and 30 minutes. After cooling the reaction mixture to room temperature, water 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate] to obtain 2.4 g of benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate as a light yellow solid.

1. temperatureby heating
2. temperatureto reflux under a nitrogen atmosphere for 4 hours
3. temperatureby heating
4. temperatureto reflux under a nitrogen atmosphere for 5 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate]