Hydrochloric Acid → HCID 22221006, compound

Participants

Reaction Steps

To a solution of ethyl 5-(2,5-dichlorophenyl)isoxazole-4-carboxylate (6.40 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.5 M toluene solution, 33 ml) at 0° C., and the mixture was stirred at room temperature for 1 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. The residue was subjected to silica gel column chromatography, and 5-(2,5-dichlorophenyl)-4-isoxazolylmethanol (3.86, yield 71%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio) and recrystallized from isopropyl ether-hexane to give a colorless prism. melting point: 51–52° C.

Provenance & Evidence