Hexane → (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane

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Reaction Steps

In a nitrogen atmosphere, (5-methyl-2-thienylethynyl)trimethylsilane (1.0 g, 5.2 mmol) was added to a hexane solution (1.0 mol/L) containing diisobutylaluminum (6.0 ml, 6.0 mmol), followed by stirring at room temperature for 24 hours. The mixture was added to a tetrahydrofuran solution, which contained Pd(PPh3)4 (0.3 g, 0.26 mmol), zinc chloride (1.0 g, 7.3 mmol), and p-methoxyiodobenzene (1.7 g, 7.3 mmol), and which had independently been prepared in another container, followed by stirring in an nitrogen atmosphere at 65° C. for 24 hours. The solution obtained was cooled to room temperature, and water was then added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated sodium chloride solution and then dried with magnesium sulfate, followed by filtration. The filtrate was concentrated using a rotary evaporator. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1). Thus, (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane (1.0 g, 3.44 mmol) was obtained in a yield of 66%.

Provenance & Evidence