Ethyl bromoacetate → Diethyl 2-cyano-2-(trimethylsilylmethyl)succinate

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Reaction Steps

A solution of ethyl 3-(trimethylsilyl)-2-cyanopropionate (2.26 g, 11.4 mmol) obtained in Example 13 in THF (15 ml) was cooled on ice, and added with sodium hydride (60%, 473 mg, 11.8 mmol) under an argon atmosphere, and the mixture was stirred for 30 minutes. The reaction mixture was added with ethyl bromoacetate (1.39 ml, 12.5 mmol), the mixture was stirred for 30 minutes under ice cooling, and stirring was further continued at room temperature for 20 hours. The reaction mixture was added with saturated aqueous ammonium chloride, 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 (19:1)] to obtain diethyl 2-cyano-2-(trimethylsilylmethyl)succinate (3.22 g, 99%) mentioned in the title as colorless oil.

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