反应详情

A solution of 5-formylfuran-2-sulfonic acid sodium salt (2.97 g), and hydroxylamine hydrochloride (1.05 g) in H2O (1.35 mL) and acetic acid (21 mL) was heated at 60° C. for 4 h. After cooling to room temperature the solvent was removed in vacuo. The crude residue was triturated with Et2O (3×50 mL) and dried under high vacuum to give a crude pale brown solid. A solution of this material (3.7 g) in phosphorusoxychloride (100 mL) was heated at 60° C. for 18 h. After cooling to room temperature the mixture was partitioned between ice-water (100 mL) and EtOAc (100 mL). The aqueous layer was separated and further extracted with EtOAc (2×100 mL). The combined organic phases were washed with brine (100 mL), dried (MgSO4), filtered and evaporated to dryness in vacuo to give a crude brown oil. To a solution of this crude oil (1.6 g) in DCM (85 mL) was added tert-butylamine (1.8 mL). After stirring at room temperature for 2 days the mixture was filtered through celite, washing with DCM (2×20 mL). The filtrate was evaporated to dryness in vacuo. The resulting crude material was purified by column chromatography using EtOAc/isohexane (2:8) as eluent to give the subtitle compound as a pale yellow oil. Yield: 1.0 g.

1. customwas removed in vacuo
2. customThe crude residue was triturated with Et2O (3×50 mL)
3. customdried under high vacuum
4. customto give a crude pale brown solid
5. temperatureAfter cooling to room temperature the mixture
6. customwas partitioned between ice-water (100 mL) and EtOAc (100 mL)
7. customThe aqueous layer was separated
8. extractionfurther extracted with EtOAc (2×100 mL)
9. washThe combined organic phases were washed with brine (100 mL)
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customevaporated to dryness in vacuo
13. customto give a crude brown oil
14. filtrationwas filtered through celite
15. washwashing with DCM (2×20 mL)
16. customThe filtrate was evaporated to dryness in vacuo
17. customThe resulting crude material was purified by column chromatography