Potassium Carbonate → 4'-Benzyloxyphenyl acetylene

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Reaction Steps

Potassium carbonate (11.1 g, 80.5 mmol) was added to a solution of the (4-benzyloxy-phenylethynyl)trimethylsilane 101 (13, from above) in methanol (70 mL). The mixture stirred at room temperature for 16 h and was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford a dark brown solid. This material was purified via column chromatography (eluting with 0-5% ethyl acetate-hexane) to afford 1-benzyloxy-4-ethynyl-benzene 102a as an off-white solid.

Provenance & Evidence