Reaktion #332239

Reaktionsgleichung

Sodium azide

4,7-dioxabicyclo[4.1.0]heptane

ammonium chloride

→

title compound

Ausbeute 41.0%

trans-4-Azidotetrahydropyran-3-ol

Ausbeute 41.0%

Lösungsmittel

water

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled to room temperature
2. 2
   SonstigeThe methanol is removed in vacuo
3. 3
   Extraktionthe remaining aqueous layer is extracted with EtOAc (3×)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo

Vorschrift

Sodium azide (50.4 g, 775 mmol) is added to a stirring solution of 4,7-dioxabicyclo[4.1.0]heptane (9.7 g, 96.9 mmol) and ammonium chloride (23.0 g, 426 mmol) in methanol (484 mL) and water (97 mL), and heated to 65° C. under nitrogen for 18 h. The mixture is cooled to room temperature and water (200 mL) is added. The methanol is removed in vacuo and the remaining aqueous layer is extracted with EtOAc (3×). The organic portions are combined, dried over sodium sulfate, filtered, and concentrated in vacuo to yield the title compound as a tan oil (5.63 g, 41%). 1H NMR (400 MHz, DMSO-d6) δ 5.40-5.33 (m, 1H), 3.78-3.74 (m, 2H), 3.40-3.32 (m, 3H), 2.97-2.90 (m, 1H), 1.82-1.77 (m, 1H), 1.46-1.41 (m, 1H).

Quelle