Potassium Phosphate, Tribasic → [4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-4-yl]-acetic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

Degassed N,N-dimethylformamide (0.37 mL) was added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 24-(1); 35.3 mg, 0.0582 mmol), 4-bromo-phenyl-acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 18.6 mg, 0.812 mmol), tetrakis(triphenylphosphine)palladium (0) (9.1 mg, 0.0079 mmol) and potassium phosphate (26.9 mg, 0.127 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 87 to 94° C. for three hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=50/1) to give the title compound (31.5 mg, 86%).

Provenance & Evidence