반응 #5490

반응 방정식

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

boron trifluoride etherate

→

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

용매

methylene chloride

반응 조건

후처리

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

실험 절차

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.

출처