Hydrochloric Acid → HCID 22221372, compound

Participants

Reaction Steps

To a solution of methyl 3-[5-(4-chloro-3-methylphenyl)-4-isoxazolyl]propionate (1.20 g) in tetrahydrofuran (40 ml) was gently added diisobutylaluminum hydride (1.0 M toluene solution, 9.5 ml) at 0° C., and the mixture was stirred at room temperature for 3 hr. Water was carefully added to the reaction mixture, acidified with dilute hydrochloric acid and 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 the crystals obtained from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio) were recrystallized from ethyl acetate-hexane to give a colorless needle of 3-[5-(4-chloro-3-methylphenyl)-4-isoxazolyl]propan-1-ol (780 mg, yield 72%). melting point: 50–51° C.

Provenance & Evidence