Triphenylphosphine → 2-Methyl-4-((trimethylsilyl)ethynyl)pyridine

Beteiligte Stoffe

Reaktionsschritte

4-Iodo-2-methyl-pyridine (9.5 g, 41.8 mmol) was dissolved in 150 mL dry THF and 18 mL triethyl amine. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (341 mg, 1.25 mmol) and bis(triphenylphosphine)palladium(II)chloride (1.47 g, 2.09 mmol) were added and the reaction mixture was stirred at RT for 1 h. Copper(I)iodide (248 mg, 1.3 mmol) and trimethylsilylacetylen (6.39 g, 6.50 mmol) were added. The reaction mixture was stirred at RT overnight. The solvent was evaporated. The residue was taken up in 500 mL water and extracted three times with ethyl acetate (500 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate gradient 100:0→0:100). The desired product was obtained as a light brown liquid (8.18 g, 99%).

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