Hydrochloric Acid → 2-Amino-6-benzoxazolemethanol

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).

1. additionTo the reaction mixture was dropwise added
2. additionwas added to a resulting mixture
3. customthe isolated precipitate was removed by filtration
4. washThe separated organic layer from filtrate was washed with brine
5. dry with materialdried over magnesium sulfate
6. customEvaporation of a solvent
7. customgave a residue, which
8. customwas purified by a column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V)
9. additionThe eluted fractions containing the desired product
10. customwere collected
11. customevaporated in vacuo

ORD record

ord-1e809c5e10cd4008b88f5fd137d16448

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05047411