Water → Tert-butyl {2-[16-(tert-butyl-dimethylsilanoxy)-hexadecynyl]-4-methoxyp henyl}-carbamate

Participants

Reaction Steps

A mixture of tert-butyl-hexadecane-15-ynyloxy-dimethylsilane (757 mg, 2.15 mmol, 1.5 eq), tert-butyl (2-iodo-4-methoxyphenyl)carbamate (500 mg, 1.43 mmol, 1 eq), [Pd(PPh3)2Cl2] (45 mg, 0.064 mmol, 0.05 eq), CuI (12 mg, 0.064 mmol, 0.05 eq), and Et3N(5 mL) was refluxed for 24 hours. Water (50 mL) and AcOEt (60 mL) were added to the reaction mixture, and the solution was filtered through celite. The filtrate was extracted three times with AcOEt (100 mL). The extract was washed with aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting concentrate was subjected to silica gel flush chromatography (eluate: hexane-AcOEt=98-2) to obtain pale yellow liquid of the title compound (754 mg, yield 92%).

Provenance & Evidence