反应详情

温度

75 °C

To a solution of 4-ethyl-2-hydroxy-5-nitrohexane nitrile (1.7 g) in t-butanol (6.8 ml) was added conc. sulfuric acid (0.8 ml) at 0° C. with stirring. After stirring for an hour at room temperature, the mixture was heated at 75° C. for an hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed successively with water and brine, dried over magnesium sulfate, and then evaporated to dryness in vacuo. The resulting oil was dissolved in acetic acid (9 ml) and chromium trioxide (0.82 g) was added thereto. The resulting mixture was heated at 100° C. for 1.5 hours, with stirring, concentrated, diluted with water, and then extracted with ethyl acetate. The extract was washed successively with water and brine, and then dried over magnesium sulfate. Removal of the solvent gave an oil which was purified by a preparative thin layer chromatography (solvent: chloroform) to give N-t-butyl-4-ethyl-5-nitro-2-oxo-hexanamide (0.46 g).

1. stirringAfter stirring for an hour at room temperature
2. extractionextracted with ethyl acetate
3. washThe extract was washed successively with water and brine
4. dry with materialdried over magnesium sulfate
5. customevaporated to dryness in vacuo
6. dissolutionThe resulting oil was dissolved in acetic acid (9 ml)
7. additionchromium trioxide (0.82 g) was added
8. temperatureThe resulting mixture was heated at 100° C. for 1.5 hours
9. stirringwith stirring
10. concentrationconcentrated
11. additiondiluted with water
12. extractionextracted with ethyl acetate
13. washThe extract was washed successively with water and brine
14. dry with materialdried over magnesium sulfate
15. customRemoval of the solvent
16. customgave an oil which
17. customwas purified by a preparative thin layer chromatography (solvent: chloroform)