Diethylamine → HCID 15087631, compound

Participants

Reaction Steps

To 75 ml of diethylamine was added with stirring 3.76 g of 4-pentynoic acid, 22 g of 2,4-diiodothiophene, and 300 mg of tetrakis-(triphenylphosphine)palladium(o). The slurry was degassed with argon and 960 mg of CuI was added. The slurry was maintained under argon and allowed to stir overnight, producing a dark brown solution. Thereafter, the solvent was removed under reduced pressure and 100 ml of 10% HCl was added to the residue. The residue was filtered and then extracted 3 x with ethyl acetate. The combined extracts were washed 1 x with water, dried over anhydrous MgSO4, filtered, and stripped. The resulting residue was flash chromatographed on a column of silica gel. Elution with a mixture of 30/70/2 parts ethyl acetate/hexane/acetic acid produced 3.5 g of the titled product as a yellow solid.

Provenance & Evidence