Reacción #5490

Ecuación de reacción

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

boron trifluoride etherate

→

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

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction is then quenched with saturated ammonium chloride
2. 2
   Extracciónextracted several times with methylene chloride
3. 3
   SecadoThe combined organic layers are dried (MgSO4)
4. 4
   Otrothe solvent is evaporated
5. 5
   OtroThe product is purified by silica gel chromatography (20% ethyl acetate/hexane)

Procedimiento

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.

Fuente