Dimethylformamide → 5-tert-Butylfuran-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (26.75 g, 0.174 mol) was added dropwise to dimethylformamide (12.92 g, 0.177 mol). This mixture was cooled to 10° C. for 1/2 hour, then 2-t-butylfuran (18.45 g, 0.149 mol) was added dropwise and the mixture stirred at room temperature for 3 hours. The mixture was poured into ice/water, neutralised with sodium carbonate and extracted into diethyl ether. The ethereal extracts were washed with water, dried over anhydrous sodium sulphate and the solvent removed to give a brown oil. Purification by column chromatography (silica eluted with petroleum ether/ethyl acetate 9:1) gave 5-t-butyl-2-furancarboxaldehyde (22.46 g, 99%).

Provenance & Evidence