General procedure for the synthesis of 4-pentylphenylacetylene from trimethyl((4-pentylphenyl)ethynyl)silane: To a solution of tetrahydrofuran (THF, 6 mL) of trimethyl((4-pentylphenyl)ethynyl)silane (900 mg, 3.68 mmol) was added a solution of tetra-n-butylammonium fluoride (n-Bu4NF) in THF (1.0 M, 0.37 mL). The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by rotary evaporator and the resulting residue was purified by silica gel column chromatography using hexane as eluent to afford 4-pentylphenylacetylene (615 mg, 97% yield) as a light yellow oil. The product was characterized by 1H NMR (CDCl3): δ 7.42 (d, J=8.3 Hz, 2H), 7.14 (d, J=8.3 Hz, 2H), 3.04 (s, 1H), 2.61 (t, J=7.8 Hz, 2H), 1.65-1.57 (m, 2H), 1.36-1.26 (m, 4H), 0.90 (t, J= 6.6Hz, 3H).
