Reaktion #499868

Reaktionsgleichung

2-naphth-2-ylethanol

hydrochloric acid

undec-7-ene

triphenylphosphine

diphenylphosphoryl azide

→

2-naphth-2-ylethylamine hydrochloride

Ausbeute 75.0%

Lösungsmittel

DMF

water

ethanol

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between water and diethyl ether
2. 2
   SonstigeThe aqueous layer was separated
3. 3
   Extraktionextracted with diethyl ether
4. 4
   WaschenThe combined organic layers were washed with 3N hydrochloric acid
5. 5
   Trocknensaturated sodium bicarbonate, dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated by rotary evaporation
8. 8
   workup.DISSOLUTIONThe residue was dissolved in THF (5 mL)
9. 9
   workup.STIRRINGstirred 3 hours
10. 10
    Sonstigeto give a precipitate
11. 11
    workup.DISSOLUTIONto dissolve the precipitate
12. 12
    workup.ADDITIONadded slowly
13. 13
    Sonstigeto give a white precipitate
14. 14
    SonstigeThe while precipitate was isolated by filtration
15. 15
    Waschenwashed with diethyl ether
16. 16
    Sonstigedried under vacuum

Vorschrift

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);

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