Hydrochloric Acid → HCID 69561763, compound

Participants

Reaction Steps

To a solution of methyl 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propionate (1.60 g) in tetrahydrofuran (60 ml) was gently added diisobutylaluminum hydride (0.95 M toluene solution, 15.2 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 the crystals obtained from a fraction eluted with acetone-hexane (1:1, volume ratio) were recrystallized from ethyl acetate-hexane to give 3-[5-(4-methylthiophenyl)-4-isoxazolyl]propan-1-ol as a colorless prism crystal (1.36 g, yield 95%). melting point: 54–55° C.

Provenance & Evidence