Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-1,3-thiazole

Participants

Reaction Steps

A solution of thiazole-2-carbaldehyde (100 g, 0.88 mol), ethane-1,2-diol (164 g, 2.65 mol), p-toluenesulfonic acid monohydrate (50 g, 0.26 mol) in toluene (1000 mL) was refluxed overnight with azetropic removal of water. The mixture was cooled to rt, diluted with ether (1000 mL), and washed with sat. NaHCO3 solution (200 mL), brine (200 mL), dried (Na2SO4), and concentrated to give a yellow oil. Flash column chromatography (petroleum ether:EtOAc, 100:1 to 50:1) afforded 2-(1,3-dioxolan-2-yl)thiazole (185 g, 66%). 1H NMR (CDCl3, 300 MHz) δ 7.75 (s, 1H), 7.31 (s, 1H), 6.09 (s, 1H), 4.04 (m, 4H).

Provenance & Evidence