Methyl iodide → Ethyl 2-(4-cyanophenyl)propanoate

Participants

Reaction Steps

Ethyl 2-(4-cyanophenyl)acetate (4.0 g, 21.14 mmol) in tetrahydrofuran (20 mL) was added to a suspension of 60% sodium hydride (850 mg, 21.14 mmol) in tetrahydrofuran (20 mL) at 0° C. and stirred for 30 min. Methyl iodide (1.36 mL, 21.14 mmol) was added at 0° C.; reaction mixture was then stirred at room temperature for 4 h. Reaction mixture quenched with saturated NH4Cl solution (20 mL), diluted with water (200 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers was washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, and evaporated to get crude, which was purified by column chromatography (silica gel; 60-120 mesh); the product eluted with 10% ethyl acetate in pet ether to yield ethyl 2-(4-cyanophenyl)propanoate (3.2 g, 75%) as colorless liquid.

Provenance & Evidence