Dimethylformamide → 2-Benzofurancarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

2.18 g of benzofuran was dissolved in 40 ml of anhydrous tetrahydrofuran. Thereto was dropwise added 12.3 ml of 1.5 M n-butyllithium hexane solution, in 5 minutes with stirring at -50° C. The mixture was stirred at 0° C. for 30 minutes and then cooled to -60° C. Thereto was added 1.61 g of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed by distillation under reduced pressure. The residue was mixed with 50 ml of ethyl acetate and 20 ml of water to dissolve the residue. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: n-hexane/ethyl acetate =20/1 to 10/1) to obtain 1.70 g (yield: 63%) of 2-benzofurancarbaldehyde as a colorless oily material.

Provenance & Evidence