Hydrochloric Acid → Ethyl 4-trimethylsilyl-3-cyanobutanoate

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl 2-cyano-2-(trimethylsilylmethyl)succinate (592 mg, 2.08 mmol) in dimethylformamide (DMF, 5 ml) was added with water (45 μl, 2.50 mmol) and lithium bromide (217 mg, 2.49 mmol), and the mixture was stirred at 150° C. for 15 hours. The reaction mixture was cooled on ice, and added with aqueous hydrochloric acid (1 N), and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and then dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)] to obtain ethyl 4-trimethylsilyl-3-cyanobutanoate (404 mg, 91%) mentioned in the title as colorless oil.

Provenance & Evidence