Ethylene Glycol → 2-(Furan-3-yl)-1,3-dioxolane

Participants

Reaction Steps

To a solution of furan-3-carbaldehyde (SM1-A, 2 g, 20 mmol) and ethane-1,2-diol (3.72 g, 60 mmol) in toluene (100 ml) was added pyridinium p-toluenesulfonate (PPTS, 50 mg, 0.2 mmol), and the solution was heated at reflux utilizing a Dean-Stark trap. After the theoretical amount of water was collected, the solvent was evaporated, and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to give product (2-A) (1.8 g, 80%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.54 (s, 1H), 7.41-7.40 (t, 1H), 6.47-6.46 (d, 1H), 5.85 (s, 1H), 4.09-4.06 (m, 2H), 4.00-3.98 (m, 2H).

Provenance & Evidence