反应详情

To a cooled (0° C.) solution of 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-ol and diphenylphosphoryl azide (9.31 g) in toluene (90 ml) was added DBU (diazabicycloundecene) (5.04 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into water, and the mixture was extracted with toluene. The combined organic layer was washed with water, dried over magnesium sulfate, and concentrated. The crude product was dissolved in a mixed solvent (77 ml) of THF/water (10:1), triphenylphosphine (9.61 g) was added, and the mixture was heated under reflux for 1 hr. After cooling to room temperature, the solvent was evaporated, 1N hydrochloric acid (100 ml) was added to the residue, and unnecessary substances were removed by extraction with ethyl acetate. The aqueous phase was alkalified with potassium carbonate, and extracted with chloroform. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated to give 1,2,2a,3,4,5-hexahydroacenaphthylen-1-ylamine.

1. extractionthe mixture was extracted with toluene
2. washThe combined organic layer was washed with water
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. dissolutionThe crude product was dissolved in a mixed solvent (77 ml) of THF/water (10:1), triphenylphosphine (9.61 g)
6. additionwas added
7. temperaturethe mixture was heated
8. temperatureunder reflux for 1 hr
9. temperatureAfter cooling to room temperature
10. customthe solvent was evaporated
11. addition1N hydrochloric acid (100 ml) was added to the residue, and unnecessary substances
12. customwere removed by extraction with ethyl acetate
13. extractionextracted with chloroform
14. washThe extract was washed with water and saturated brine
15. dry with materialdried over magnesium sulfate
16. concentrationconcentrated