Réaction #5490

Équation de réaction

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

boron trifluoride etherate

→

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

Solvants

methylene chloride

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source