Hydrochloric Acid → 3-[5-(4-Chlorophenyl)-4-isoxazolyl]propan-1-ol

Participants

Reaction Steps

To a solution of methyl 3-[5-(4-chlorophenyl)-4-isoxazolyl]propionate (6.00 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 50 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 3-[5-(4-chlorophenyl)-4-isoxazolyl]propan-1-ol (4.89 g, yield 91%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 58–59° C.

Provenance & Evidence