Reaktion #167508

Reaktionsgleichung

bromoethylmannose

sodium azide

sodium iodide

→

azidoethylmannose

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 5 L round bottom three-necked flask, equipped with a heating mantle, an overhead stirrer
2. 2
   Temperaturthe solution warmed to 50 C
3. 3
   Einengenconcentrated to dryness on the rotovap
4. 4
   FiltrationThe combined organic portions are filtered
5. 5
   Sonstigeevaporated to dryness

Vorschrift

A 5 L round bottom three-necked flask, equipped with a heating mantle, an overhead stirrer, and a thermometer, is charged with 150 gm bromoethylmannose (525 mmol). The oil is dissolved in 2 L water and treated with 68.3 gm sodium azide (1.05 mol, 2 equiv.; 65 gm/mol; Alfa-Aesar) followed by 7.9 gm sodium iodide (52.5 mmol, 0.08 equiv.; 149.89 gm/mol; Alfa-Aesar) and the solution warmed to 50 C and stirred overnight. The solution is cooled to room temperature and concentrated to dryness on the rotovap. The solid residue is digested with 3×500 mL of 5:1 vol. CHCl3:MeOH at 40 C. The combined organic portions are filtered and evaporated to dryness to afford azidoethylmannose as an off-white solid.

Quelle