Trimethylsilylacetylene → N,N-Diethyl-4-((trimethylsilyl)ethynyl)aniline

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Reaction Steps

To an oven dried flask fitted with a magnetic stir bar and condenser, Pd(PPh3)4 (207 mg, 0.18 mmol) and cuprous iodide (115 mg, 0.6 mmol) was added and the system was evacuated and back flushed with N2. Dry THF (25 mL) was added, subsequently N,N-diethyl-(4-iodophenyl)amine (1 g, 3.6 mmol in 3 mL THF) and dry degassed diisopropylethylamine (2.5 mL, 14.5 mmol) stirred for 10 min. Trimethylsilylacetylene (0.85 mL, 6 mmol) was added and the mixture was stirred at room temperature for 4 h and then at 80° C. for 30 min. The reaction mixture was cooled to room temperature, poured into ice water and stirred at rt for 1 h. The mixture was extracted with ethyl acetate (50×3), the combined organic layer was washed with saturated ammonium chloride solution and was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation and the crude product was purified by silica gel column chromatography using hexane/EAC (0-5%) as eluent. Yield: 0.54 g. (61%). IR (neat) 2958, 2857, 2145, 1605, 1515, 1468, 1401 cm−1; 1H NMR (400 MHz, CDCl3) 7.37 (d, J=8.8 Hz, 2H), 6.57 (d, J=8.8 Hz, 2H), 3.37 (q, 7.2 Hz, 4H), 1.19 (t, 6.8 Hz, 6H), 0.32 (s, 9H); 13CNMR (100 MHz, CDCl3) δ 147.41, 133.14, 110.81, 108.66, 106.77, 90.43, 44.09, 12.35.

Provenance & Evidence