تفاعل #499868

معادلة التفاعل

2-naphth-2-ylethanol

hydrochloric acid

undec-7-ene

triphenylphosphine

diphenylphosphoryl azide

→

2-naphth-2-ylethylamine hydrochloride

المردود 75.0%

المذيبات

DMF

water

ethanol

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىpartitioned between water and diethyl ether
2. 2
   أخرىThe aqueous layer was separated
3. 3
   استخلاصextracted with diethyl ether
4. 4
   غسيلThe combined organic layers were washed with 3N hydrochloric acid
5. 5
   تجفيفsaturated sodium bicarbonate, dried (MgSO4)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated by rotary evaporation
8. 8
   workup.DISSOLUTIONThe residue was dissolved in THF (5 mL)
9. 9
   workup.STIRRINGstirred 3 hours
10. 10
    أخرىto give a precipitate
11. 11
    workup.DISSOLUTIONto dissolve the precipitate
12. 12
    workup.ADDITIONadded slowly
13. 13
    أخرىto give a white precipitate
14. 14
    أخرىThe while precipitate was isolated by filtration
15. 15
    غسيلwashed with diethyl ether
16. 16
    أخرىdried under vacuum

الإجراء التجريبي

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);

المصدر