Hydrochloric Acid → 2-(2-Thienyl)-5-benzoxazolylmethanol

Participants

Reaction Steps

To a solution of methyl 2-(2-thienyl)-5-benzoxazolecarboxylate (1.50 g) in tetrahydrofuran (30 ml) was slowly added lithium aluminum hydride (220 mg) at 0° C., stirred for 30 minutes. To the reaction mixture was added water, which was made acidic with 1N-hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (4:1, v/v), 2-(2-thienyl)-5-benzoxazolyl methanol (1.03 g, 77%) was obtained. The recrystalization from ethyl acetate-hexane gave colorless needles, mp 158-159° C.

Provenance & Evidence