反应 #5490

反应方程式

Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

boron trifluoride etherate

→

ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他The reaction is then quenched with saturated ammonium chloride
2. 2
   萃取extracted several times with methylene chloride
3. 3
   干燥The combined organic layers are dried (MgSO4)
4. 4
   其他the solvent is evaporated
5. 5
   其他The product is purified by silica gel chromatography (20% ethyl acetate/hexane)

实验过程

Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate (0.98 g, 2.98 mmol) is dissolved in methylene chloride (50 mL), and boron trifluoride etherate (1.8 mL, 15 mmol) is added. The reaction is stirred at room temperature for 26 hours. The reaction is then quenched with saturated ammonium chloride and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (20% ethyl acetate/hexane) to give ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 91°-92° C.

来源