1-Iodonaphthalene → 3-(1-Naphthyl)-2-propyn-1-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of de-gassed 1-iodonaphthalene (10.00 g, 39.36 mmol), propargyl alcohol (2.25 g, 40.15 mmol, 1.02 eq.), triethylamine (7.97 g, 78.72 mmol, 2 eq.) and copper iodide (0.02 g, 0.12 mmol, 0.3 mol %) in tetrahydrofuran (30 mL) was added bis(triphenylphosphine)palladium(II) chloride (0.05 g, 0.07 mmol, 0.18 mol %). The mixture was stirred at 35° C. under an atmosphere of nitrogen for 19 h. The mixture was concentrated in vacuo to afford a black tar residue. The residue was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 30%:70%) to afford the desired compound as a yellow oil (3.51 g, 49%). 1H NMR (400 MHz, CDCl3) δ ppm 4.64 (2H, s, CH2), 7.38-7.40 (3H, m, ArH), 7.64 (1H, m, ArH), 7.79 (1H, d, J=8.0 Hz, ArH), 7.81 (1H, d, J 8.0 Hz, ArH), 8.32 (1H, d, J 8.0 Hz, ArH).

Provenance & Evidence