Hydrochloric Acid → HCID 69560923, compound

Participants

Reaction Steps

To a solution of ethyl 5-(4-methylthiophenyl)isoxazole-4-carboxylate (10.0 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (0.95 M hexane solution, 92 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 obtained crystals were recrystallized from ethyl acetate-isopropyl ether to give 5-(4-methylthiophenyl)-4-isoxazolylmethanol (7.50 g, yield 89%) as a colorless prism. melting point: 102–103° C.

Provenance & Evidence