Hydrochloric Acid → (2E)-3-[4-(4-fluorophenyl)-1,2,3-thiadiazol-5-yl]acrylic acid

Participants

Reaction Steps

A mixture of 4-(4-fluorophenyl)-1,2,3-thiadiazole-5-carbaldehyde (180 mg), ethyl diethylphosphonoacetate (450 mg), sodium hydride (60% in oil, 40 mg) and N,N-dimethylformamide (3 ml) was stirred at room temperature for 2 hrs. The reaction mixture was poured into a 1N aqueous hydrochloric acid solution and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated, and a 6N aqueous hydrochloric acid solution (3 ml) and acetic acid (3 ml) were added to the residue. The mixture was stirred for 3 hrs. with heating under reflux. The reaction mixture was concentrated and poured into water. The precipitated solids were collected by filtration, washed with water and dried to give (2E)-3-[4-(4-fluorophenyl)-1,2,3-thiadiazol-5-yl]acrylic acid (130 mg, yield 60%) as a pale-yellow solid.

Provenance & Evidence