Tetrahydrofuran → 3-phenyl-2(5H)-furanone

Participants

Reaction Conditions

Reaction Steps

3-Iodo-3-phenyl-prop-2-en-1-ol (Description 1; 1 g, 3.8 mM) was dissolved in tetrahydrofuran (20 ml) and Hunig's base (2.67 ml, 15.4 mM) and degassed using a Firestone valve (×3). Carbon monoxide was bubbled through the solution for 10 minutes after which tris(dibenzylideneacetone)dipalladium (141 mg; 4 mol %) and 1,4 bis(diphenylphosphino) butane (65 mg; 4 mol %) were added. The reaction was heated at 50° C. under an atmosphere of carbon monoxide. After 2 hours, when the reaction was 50% complete, an extra addition of the palladium source and phosphine ligand were made. After a further 2 hours the reaction was cooled, filtered, the solvent removed in vacuo and the residue was dispersed between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (2×40 ml), the combined organic layers were washed with brine, dried over MgSO4 and the solvent removed in vacuo. Purification was carried out by silica chromatography eluting in increasing concentrations of ethyl acetate in hexane (0-15%) to afford the title compound as a tan-coloured solid (0.56 g, yield 91%).

Provenance & Evidence