反应详情

Zinc dust (28.0 g, 428 mmol) was added to a suspension of (E)-5-bromo-2,3-dihydro-1H-inden-1-one oxime (19.4 g, 86 mmol) in acetic acid (30 mL). The suspension was stirred at rt for 48 h. The reaction was filtered over Kiezelguhr gel. The residue was rinsed with ethyl acetate (2×100 mL). The combined filtrates were concentrated under reduced pressure to obtain a yellow oil. The yellow oil was partitioned between ethyl acetate (200 mL) and 2 N aq. HCl (200 mL). The acidic layer was separated before being basified using aq. 4 N NaOH and a white suspension was formed. Ethyl acetate (200 mL) was added and the milky mixture was filtered over Kiezelguhr gel. The organic phase was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as a clear light yellow oil (10.8 g, 59%). MS (ESI): m/z [M−NH2]+ 198.0

1. filtrationThe reaction was filtered over Kiezelguhr gel
2. washThe residue was rinsed with ethyl acetate (2×100 mL)
3. concentrationThe combined filtrates were concentrated under reduced pressure
4. customto obtain a yellow oil
5. customThe yellow oil was partitioned between ethyl acetate (200 mL) and 2 N aq. HCl (200 mL)
6. customThe acidic layer was separated
7. customa white suspension was formed
8. filtrationthe milky mixture was filtered over Kiezelguhr gel
9. customThe organic phase was separated
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure