Dimethylformamide → 5-Phenylthiophene-2-carbaldehyde

Participants

Reaction Steps

Under a nitrogen atmosphere 35 mL of dimethylformamide was cooled to 0° C. and 7 mL of phosphorus oxychloride was added with stirring. The solution was allowed to warm to ambient temperature, and then a solution of 10.0 grams (0.0625 mole) of 2-phenylthiophene in 10 mL of dimethylformamide was added in one portion. The reaction mixture was heated to 80° C. where it stirred for 24 hours and then poured into 250 mL of an aqueous 10% sodium hydroxide solution containing 50 grams of ice. The resulting slurry was extracted with diethyl ether, and the extract was washed in succession with water, an aqueous solution saturated with sodium chloride, and water. The organic layer was concentrated under reduced pressure to a solid residue which was dried under high vacuum to yield 6.8 grams of 5-formyl-2-phenylthiophene.

Provenance & Evidence