تفاعل #5490

معادلة التفاعل

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

boron trifluoride etherate

→

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

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر