Ethyl bromoacetate → 3-Cyano-3-(3,4-dimethoxyphenyl)pentanedioic diethyl ester

Participants

Reaction Conditions

Reaction Steps

Combine 3,4-dimethoxyphenylacetonitrile (20 g, 113 mmol) and anhydrous tetrahydrofuran (100 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of sodium bis(trimethylsilyl)amide (226 mL, 1M in tetrahydrofuran, 226 mmol). When the addition is complete warm the reaction mixture to 10° C. and allow to stir for 15 minutes. Cool in a dry-ice/acetone bath, add dropwise ethyl bromoacetate (37.7 g, 226 mmol). When the addition of ethyl bromoacetate is complete, warm the reaction mixture to ambient temperature. After 18 hours, partition the reaction mixture between diethyl ether and water. Extract the organic layer with water and saturated aqueous solution of ammonium chloride. Separate the organic layer, dry over MgSO4, filter, and concentrate invacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 33% ethyl acetate/hexane. Remove residual solvent invacuo at 82° C. to give the title compound: Rf =0.37 (silica gel, 33% ethyl acetate/hexane). Elemental Analysis calculated for C18H23NO6 : C 61.88; H 6.64; N 4.01; Found: C 61.79; H 6.62; N 3.91.

Provenance & Evidence