反応 #567395

反応方程式

dihydroartemisinin

boron trifluoride

→

9,10-anhydrodehydroartemisinin

収率 172.5%

溶媒

diethyl ether

反応条件

後処理

1. 1
   洗浄washed with 5% NaHCO3 solution (3×100 ml)
2. 2
   乾燥dried (MgSO4)
3. 3
   濃縮concentrated in vacuo
4. 4
   その他The residue was then purified by flash chromatography (SiO2; 10% ethyl acetate/hexanes)

実験手順

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).

出典