Reaktion #480191

Reaktionsgleichung

undec-7-ene

1H-indole-4-methanol

diphenylphosphoryl azide

→

4-(azidomethyl)-1H-indole

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath was removed
2. 2
   SonstigeThe solvent was evaporated
3. 3
   workup.ADDITIONethyl acetate was added
4. 4
   WaschenThe solution was washed with 1 M HCl and brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigechromatographed (12% ethyl acetate/hexanes)

Vorschrift

To a solution of 1H-indole-4-methanol (71 mg, 0.48 mmol) in tetrahydrofuran (1 mL) at 0° C. was added diphenylphosphoryl azide (156 μL, 0.72 mmol) followed by 1,8-diaza[5.4.0]undec-7-ene (87.4 μL, 0.58 mmol). The cooling bath was removed and the solution was allowed to stir for 5 h. The solvent was evaporated and ethyl acetate was added. The solution was washed with 1 M HCl and brine, dried (MgSO4), filtered, concentrated and chromatographed (12% ethyl acetate/hexanes) to give 4-(azidomethyl)-1H-indole (1.496 g, 88%) as an oil.

Quelle