反应详情

A mixture of 0.9 g (5.63 mmol) of 2,3-dihydro-4-ethyl-1H-inden-1-one and 20 g of trichloroacetic acid was heated at 60°-65° for 30 minutes. To this was added 2.5 g (38.3 mmol) of sodium azide and the mixture was heated at 60°-65°, under nitrogen, for 18 hours. It was poured into 200 ml of ice water and extracted with methylene chloride. The organic layer was washed with saturated sodium hydrogen carbonate, saturated sodium chloride, dried (MgSO4), and concentrated. The residue was chromatographed (SiO2) using a gradient from pure methylene chloride to 19:1 methylene chloride-methanol to give a solid which was rechromatographed using 98:1 methylene chloride-methanol. Recrystallization from toluene/hexane gave 0.21 g (21%) of product; mp 123°-126°.

1. temperaturewas heated at 60°-65° for 30 minutes
2. temperaturethe mixture was heated at 60°-65°, under nitrogen, for 18 hours
3. extractionextracted with methylene chloride
4. washThe organic layer was washed with saturated sodium hydrogen carbonate, saturated sodium chloride
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customThe residue was chromatographed (SiO2)
8. customto give a solid which
9. customwas rechromatographed
10. customRecrystallization from toluene/hexane