Hydrochloric Acid → HCID 22220967, compound

Participants

Reaction Steps

A mixture of dibenzoylmethane (4.48 g), methyl acrylate (1.8 ml), potassium t-butoxide (0.23 g) and N,N-dimethylformamide (40 ml) was stirred at room temperature overnight. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and a colorless oil was obtained from a fraction eluted with ethyl acetate-hexane (1:9, volume ratio). A mixture of the obtained colorless oil, hydroxylamine hydrochloride (1.00 g) and isopropyl alcohol (50 ml) was refluxed for 6 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a colorless oil. A mixture of the obtained colorless oil, 2N sodium hydroxide (20 ml) and methanol (30 ml) was stirred at room temperature for 2 hr. The reaction mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were filtrated to give 3-[3,5-diphenyl-4-isoxazolyl]propionic acid (1.91 g, yield 33%). The crystals were recrystallized from ethanol. melting point: 152–153° C.

Provenance & Evidence