Sodium Iodide → HCID 18443687, compound

Participants

Reaction Steps

A solution of 4-phenylphenol (0.774 g, 4.55 mmol) and potassium tert-butoxide (0.51 g, 4.55 mmol) in toluene (20 mL) was stirred for 1 h at room temperature. Sodium iodide (0.068 g, 0.45 mmol) and toluene-4-sulfonic acid but-3-ynyl ester (1.02 g, 4.55 mmol) were added, and the mixture heated to reflux for 24 hours. The mixture was cooled to room temperature, diluted with diethyl ether (20 mL), washed with water (2×20 mL). The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.57) to give an oil (140 mg, 14%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.50 (m, 4H), 7.46–7.38 (m, 2H), 7.32 (d, 1H, J=7.3), 7.02–6.95 (m, 2H), 4.15 (t, 2H, J=7.0), 2.71 (dt, 2H, J=2.7, 7.3), 2.06 (t, 1H, J=2.7).

Provenance & Evidence