Water → 5-(4-Chloro-phenoxy)-furan-2-carbaldehyde

Participants

Reaction Steps

To a solution of 4-chlorophenol (4.4 g, 33.6 mmol) in dimethylsulfoxide (30 mL) was added sodium hydride (1.34 g, 33.6 mmol, 60% in oil), and the solution was stirred at room temperature for 10 minutes. 5-Nitrofuran-2-carbaldehyde (4.0 g, 28 mmol) was added to this reaction solution, and the solution was stirred at room temperature for 5 minutes. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed with water 6 times. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane, then hexane:ethyl acetate=10:1, then 4:1), and the title compound (3.3 g, 14.9 mmol, 53.0%) was obtained as a yellow oil.

Provenance & Evidence