Reaktion #518643

Reaktionsgleichung

methyl iodide

Sodium hydride

tert-butyl 2-(2-azidoethoxy)ethylcarbamate

sodium hydride

→

tert-butyl 2-(2-azidoethoxy)ethyl(methyl)carbamate

Ausbeute 94.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with hexanes (3×) under N2
2. 2
   workup.ADDITIONThe dried sodium hydride was treated with 800 mL of anhydrous THF
3. 3
   workup.ADDITIONAfter addition
4. 4
   workup.STIRRINGAfter stirring overnight
5. 5
   Sonstigethe reaction was quenched with 300 mL of saturated NaHCO3 solution
6. 6
   workup.ADDITIONThe reaction mixture was then treated with 200 mL of H2O and 1 L of Et2O
7. 7
   SonstigeThe organic phase was separated
8. 8
   Waschenwashed with H2O and brine
9. 9
   TrocknenThe organic portion was then dried over MgSO4
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

Sodium hydride (60% oil dispersion, 9.1 g, 228 mmol) was placed in a round bottom flask and washed with hexanes (3×) under N2. The dried sodium hydride was treated with 800 mL of anhydrous THF. A solution of tert-butyl 2-(2-azidoethoxy)ethylcarbamate (41.9 g, 182 mmol) in 200 mL of THF was then added to the stirred sodium hydride solution over 40 min. After addition was complete, the reaction was stirred an additional 20 min followed by addition of methyl iodide (13.6 mL, 218 mmol). After stirring overnight, the reaction was quenched with 300 mL of saturated NaHCO3 solution. The reaction mixture was then treated with 200 mL of H2O and 1 L of Et2O. The organic phase was separated and washed with H2O and brine. The organic portion was then dried over MgSO4 and concentrated under reduced pressure to give 41.9 g of tert-butyl 2-(2-azidoethoxy)ethyl(methyl)carbamate as a yellow liquid.

Quelle