Hydrochloric Acid → 2-Amino-6-benzoxazolemethanol

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Reaction Steps

A solution of 2-amino-6-ethoxycarbonylbenzoxazole (14.3 g) in tetrahydrofuran (570 ml) was dropwise added to a mixture of lithium aluminum hydride (7.9 g) in tetrahydrofuran (300 ml) at -30° C. to -20° C. for 35 minutes, and the mixture was stirred for 75 minutes at the same temperature. To the reaction mixture was dropwise added a mixture of water (3 ml) and tetrahydrofuran (3 ml), and the mixture of ethyl acetate and water was added to a resulting mixture. The mixture was adjusted to pH 7 with 6N-hydrochloric acid and the isolated precipitate was removed by filtration. The separated organic layer from filtrate was washed with brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by a column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-amino-6-hydroxymethylbenzoxazole (5.77 g).

Provenance & Evidence