反应详情

温度

65 °C

A solution comprising 2-naphth-2-ylethanol (0.5 g, 2.9 mmol) in dry DMF (5 mL) was combined under nitrogen with diphenylphosphoryl azide (0.74 mL, 3.42 mmol) and 1,8-diazaabicyclo[5.4.0]undec-7-ene (0.47 mL. 3.14 mmol). The mixture was heated at 65° C. for 3 hours and then partitioned between water and diethyl ether. The aqueous layer was separated and extracted with diethyl ether. The combined organic layers were washed with 3N hydrochloric acid and then saturated sodium bicarbonate, dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was dissolved in THF (5 mL) and the solution was combined with triphenylphosphine (1 g, 3.81 mmol), stirred for 2 hours at room temperature, diluted with water (0.100 mL), stirred 3 hours, diluted with concentrated hydrochloric acid (0.33 mL) to give a precipitate, treated with ethanol (5 mL) to dissolve the precipitate and treated with diethyl ether, added slowly, to give a white precipitate. The while precipitate was isolated by filtration, washed with diethyl ether and dried under vacuum to provide 2-naphth-2-ylethylamine hydrochloride (0.447 g, 75% yield);

1. custompartitioned between water and diethyl ether
2. customThe aqueous layer was separated
3. extractionextracted with diethyl ether
4. washThe combined organic layers were washed with 3N hydrochloric acid
5. dry with materialsaturated sodium bicarbonate, dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. dissolutionThe residue was dissolved in THF (5 mL)
9. stirringstirred 3 hours
10. customto give a precipitate
11. dissolutionto dissolve the precipitate
12. additionadded slowly
13. customto give a white precipitate
14. customThe while precipitate was isolated by filtration
15. washwashed with diethyl ether
16. customdried under vacuum