General procedure for the synthesis of 4'-diethylaminophenylacetylene from N,N-diethyl-4-((trimethylsilyl)ethynyl)aniline: a mixture of N,N-diethyl-4-((trimethylsilyl)ethynyl)aniline (500 mg, 2.03 mmol), potassium carbonate (K2CO3, 1.5 g, 10.8 mmol), and methanol (30 mL) was reacted at 65 C for 30 hours with stirring. After completion of the reaction, the reaction mixture was cooled, poured into water and extracted with ethyl acetate (50 mL × 3). The organic extracts were combined and dried with anhydrous magnesium sulfate (MgSO4). Subsequently, the solvent was removed under reduced pressure to give the crude product. The crude product was chromatographed on a short silica gel column and further purified using a gradient elution of hexane/ethyl acetate (0-5%), and the final product was isolated as a semi-solid. Yield: 250 mg (72.2%). The product characterization data were as follows: IR (pure) 2971, 2098, 1607, 1551 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J = 8.4 Hz, 2H), 6.59 (d, J = 8.4 Hz, 2H), 3.36 (q, J = 6.8 Hz, 4H), 1.16 (t, J = 6.8 Hz. 6H); 13C NMR (100 MHz, CDCl3) δ 147.68, 133.31, 110.90, 107.46, 84.96, 74.38, 44.19, 12.41.
![Benzenamine, N,N-diethyl-4-[2-(trimethylsilyl)ethynyl]-](/CAS/20210111/GIF/562813-15-4.gif)
