反应详情

Bis(pinacolato)diboron (0.41 g), potassium acetate (0.25 g), tris(dibenzylideneacetone)dipalladium(0) (46 mg), and a 15% tricyclohexylphosphine-toluene solution (0.25 mL) were added to a dioxane (3.5 mL) solution of benzyl 2-(benzyloxy)-4-chlorobenzoate (0.35 g), followed by stirring under a nitrogen atmosphere at room temperature for 30 minutes and then at 80° C. for 5 hours and 30 minutes. After cooling the reaction mixture to room temperature, tris(dibenzylideneacetone)dipalladium(0) (46 mg) and a 15% tricyclohexylphosphine-toluene solution (0.25 mL) were added thereto, followed by stirring under a nitrogen atmosphere at 90° C. for 8 hours. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium bicarbonate 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: 100-75% hexane/ethyl acetate] to obtain benzyl 2-(benzyloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate.

1. waitat 80° C. for 5 hours
2. custom30 minutes
3. temperatureAfter cooling the reaction mixture to room temperature
4. stirringby stirring under a nitrogen atmosphere at 90° C. for 8 hours
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: 100-75% hexane/ethyl acetate]