Reaktion #567395

Reaktionsgleichung

dihydroartemisinin

boron trifluoride

→

9,10-anhydrodehydroartemisinin

Ausbeute 172.5%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 5% NaHCO3 solution (3×100 ml)
2. 2
   Trocknendried (MgSO4)
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe residue was then purified by flash chromatography (SiO2; 10% ethyl acetate/hexanes)

Vorschrift

To a solution of dihydroartemisinin (10.4 g) in diethyl ether (550 ml) at room temperature under nitrogen was added dropwise boron trifluoride dietherate (1.0 ml). The solution was stirred at room temperature overnight, washed with 5% NaHCO3 solution (3×100 ml); dried (MgSO4) and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2; 10% ethyl acetate/hexanes) to give 9,10-anhydrodehydroartemisinin as a white solid (16.8 g, 97%). δH: 6.20 (1H, q, J=1.41 Hz, H-10), 5.55 (1H, s, H-12), 2.33-3.50 (1H, m), 1.03-2.18 (10H, m), 1.60 (3H, d, J=1.41 Hz, H16), 1.44 (3H, s, H-14), 1.00 (3H, d, J=5.98 Hz, H-15).

Quelle