2-Ethynyl-naphthalene

Synthesis

Tetrabutylammonium fluoride (2.9 mL, 2.87 mmol, ca 1.0 M en THF) was added to a stirred solution of trimethyl(3-(naphth-2-yl)ethynyl)silane (534 mg, 2.39 mmol) in dry THF (25 mL), under argon. After stirring for 1 h, the reaction mixture was diluted with ethyl acetate and HCl (10%). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (x2). All the combined organic extracts were dried (anh. Na2SO4), filtered and concentrated under reduced pressure. The residue was further purified by flash chromatography eluting with hexane to yield 2-Ethynyl-naphthalene (354 mg, 98%) as a colourless oil.