Reaction #5490

Reaction equation

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

boron trifluoride etherate

→

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

Solvents

methylene chloride

Conditions

Workup

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

Procedure

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