Diethylamine → HCID 15087631, compound

Participants

Reaction Steps

To 75ml of diethylamine was added with stirring 3.76g of 4-pentynoic acid, 22g of 2,4-diiodothiophene, and 300mg of tetrakis(triphenylphosphine)palladium(o). The slurry was degassed with argon and 960mg 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 100ml of 10% HCl was added to the residue. The residue was filtered and then extracted 3x with ethyl acetate. The combined extracts were washed 1x 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