Boron trifluoride etherate → Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate
Reaction equation
C[Si]([CH2:5][C:6]1(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21])(C)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:5]=[C:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21]Participants
4
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.