Ethylene Glycol → (5-[1,3]-Dioxolan-2-yl-benzofuran-2-yl)-(4-fluoro-phenyl)-methanone

Participants

Reaction Steps

2-(4-fluorobenzoyl)-1-benzofuran-5-carbaldehyde (500 mg, 1.86 mmol) and ethylene glycol (2.31 g, 37.2 mmol) were suspended in toluene (20 mL) followed by the addition of (1S)-(+)-10-camphorsulfonic acid (30 mg). This suspension was heated under reflux for 2 hours. After allowing the reaction mixture to cool on standing, saturated aqueous sodium bicarbonate solution was poured thereinto followed by extraction with ethyl acetate. The organic layer was separated followed by washing with sat. NaCl and drying over anhydrous magnesium sulfate. The organic layer was filtered using a glass filter and the filtrate was filtered with a glass filter coated with NH-silica gel. This filtrate was concentrated under a reduced pressure to obtain (5-[1,3]-dioxolan-2-yl-benzofuran-2-yl)-(4-fluoro-phenyl)-methanone (377 mg, 65%).

Provenance & Evidence