Реакция #567395

Уравнение реакции

dihydroartemisinin

boron trifluoride

→

9,10-anhydrodehydroartemisinin

Выход 172.5%

Растворители

diethyl ether

Условия реакции

Обработка

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

Методика

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).

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