B1([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C)C=CC=CC=1.[CH2:50]([O:57][C:58]1[CH:73]=[C:72](Cl)[CH:71]=[CH:70][C:59]=1[C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:61])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(=O)(O)[O-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O1CCOCC1>[CH2:50]([O:57][C:58]1[CH:73]=[C:72]([B:10]2[O:11][C:12]([CH3:17])([CH3:18])[C:13]([CH3:15])([CH3:16])[O:14]2)[CH:71]=[CH:70][C:59]=1[C:60]([O:62][CH2:63][C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)=[O:61])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1Bis(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.
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