Реакция #5490

Уравнение реакции

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

boron trifluoride etherate

→

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

Растворители

methylene chloride

Условия реакции

Обработка

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

Методика

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.

Источник