Aluminum(III) Chloride → HCID 13588844, compound

Participants

Reaction Steps

A solution of 5.2 g (0.022 mole) of (5-isobutyl-2-thienyl)succinic anhydride in 20 cc of nitrobenzene was added drop by drop to a solution of 8 g (0.06 mole) of aluminum chloride in 40 cc of nitrobenzene. The mixture was brought to 40C for 1 hour. After cooling to ambient temperature, the reaction mixture was poured into an ice-hydrochloric acid mixture, then extracted with methylene chloride. The organic solution was extracted with an aqueous sodium carbonate solution. The aqueous phase was acidified by dilute hydrochloric acid. The oil that separated was extracted with ethyl acetate. After elimination of the solvent under reduced pressure, the residue was purified by chromatography on a silica column (9/1/0.05 methylene chloride-methanol-acetic acid eluant). 2.3 g (yield=44%) of 2-isobutyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid melting at 80° C. was obtained and used in the next stage without further purification. An analytical sample was obtained by recrystallization in a hexane-ethyl acetate mixture.

Provenance & Evidence