Ethylene Glycol → 2-(3-Thienyl)-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

To a solution of thiophene-3-carbaldehyde (25.00 g, 222.9 mmol) in toluene (250 ml) were added ethylene glycol (69.18 g, 1115 mmol) and p-toluenesulfonic acid (424.0 mg, 2.229 mmol). The mixture was heated under reflux for 4 hr while separating generated water using Dean-Stark trap. After cooling to 0° C., saturated aqueous sodium hydrogen carbonate solution (50 ml) was added, and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, filtered through silica gel pad (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g), and washed with ethyl acetate/hexane mixed solvent (1:2, 1000 ml). The filtrate was concentrated under reduced pressure to give 2-(thiophen-3-yl)-1,3-dioxolane (33.40 g, 213.8 mmol, yield 95.9%) as a yellow oil.

Provenance & Evidence