Ethylene Glycol → HCID 59300654, compound

Participants

Reaction Conditions

Reaction Steps

To a sealed tube flushed with nitrogen, was added 3-iodobenzaldehyde 31.1 (300 mg, 1.29 mmol), 4-(trifluoromethyl)benzenethiol (230 mg, 1.29 mmol), copper (I) iodide (24.6 mg, 0.129 mmol), ethylene glycol (0.144 mL, 2.59 mmol), potassium carbonate (357 mg, 2.59 mmol), and isopropanol (6.50 mL). The reaction mixture was heated at 85° C. for 48 hours. The reaction was then cooled and diluted with DCM and filtered over a pad of diatomaceous earth. The filtrate was concentrated, and the residue was purified by medium pressure chromatography (silica gel, 0 to 20% diethyl ether:hexanes) to give 31.2 (162 mg). 1H NMR (400 MHz, CDCl3) δ ppm 9.92 (1H, s), 7.85 (1H, s), 7.77 (1H, d, J=7.4 Hz), 7.59 (1H, d, J=7.8 Hz), 7.44-7.50 (3H, m), 7.29 (2H, d, J=8.2 Hz).

Provenance & Evidence