反应 #61693

反应方程式

NaHCO3

bis-(2-methoxyethyl)aminosulfur trifluoride

4a

tropenol 9-hydroxyfluorene-9-carboxylate

water

→

tropenol 9-fluorofluorene-9-carboxylate

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   温度cooled to 0° C.
2. 2
   其他the organic phase is separated off
3. 3
   萃取the aqueous phase is extracted again with dichloromethane
4. 4
   洗涤the combined organic phases are washed with water
5. 5
   干燥dried over magnesium sulfate
6. 6
   其他evaporated to dryness
7. 7
   其他The hydrochloride is precipitated
8. 8
   其他recrystallized from acetonitrile-diethyl ether

实验过程

1.66 mL (0.009 mol) of bis-(2-methoxyethyl)aminosulfur trifluoride are placed in 10 mL dichloromethane and within 20 minutes at 15°-20° C., a solution of 2.4 g (0.007 mol) of 4a in 25 mL dichloromethane is added dropwise thereto. The mixture is stirred for 20 hours at ambient temperature, cooled to 0° C., and carefully combined with 80 mL of water with thorough stirring. Then the mixture is carefully adjusted to pH 8 with aqueous NaHCO3 solution, the organic phase is separated off, the aqueous phase is extracted again with dichloromethane, the combined organic phases are washed with water, dried over magnesium sulfate, and evaporated to dryness. The hydrochloride is precipitated and recrystallized from acetonitrile-diethyl ether. Then the free base is liberated again using 10% aqueous sodium carbonate solution. Yield: 1.05 g bright yellow crystals (53% of theoretical yield).

来源