Ethylene Glycol → HCID 11448548, compound

Participants

Reaction Steps

To a solution of 5-(4-fluorophenyl)-5-oxopentanoate (2.26 g, 10 mmol) in toluene (60 ml) was added ethylene glycol (1.95 ml, 35 mmol) and p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol) and the mixture refluxed in a Dean-Stark apparatus under nitrogen for 17 h. The toluene was removed by rotary evaporator and the residue treated with sodium bicarbonate solution (5%, 50 ml) and extracted with ether (2×50 ml). The ether extract was washed with brine (1×50 ml), dried (Na2SO4) and evaporated to give methyl 4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]butanoate (9) as a pale yellow oil (2.47 g, 91%). 1H nmr (CDCl3, 300 MHz) 1.6-1.7, m, H3; 1.9, m, H4; 2.30, t (7.5 Hz), H2; 3.64, s, OMe; 3.7-3.8, m, CH2O; 3.95-4.05, m, CH2O; 7.01, m, H3′,5′; 7.41, m, H2′,6′. ESI (+ve) MS m/z 269 (M+H, 45%).

Provenance & Evidence