Sodium hydride → trans-Ethyl 2-(pyridin-4-YL)cyclopropanecarboxylate

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Reaction Steps

Trimethylsulfoxonium iodide (2.37 g, 10.8 mmol) and sodium hydride (60% in mineral oil, 0.431 g, 10.8 mmol) were combined and stirred under an atmosphere of argon. To these solids was added DMSO (40 mL) dropwise via addition funnel over 10 min. Hydrogen gas evolved and the solution turned cloudy. To this cloudy solution was added ethyl (2E)-3-pyridin-4-ylacrylate (1.42 g, 8.01 mmol) in DMSO (60 mL) dropwise over 20 min. The reaction mixture was allowed to stir at rt for 18 h. The reaction was quenched by the addition of water. The solution was diluted with Et 20 and the aqueous and organic solutions were separated. The aqueous solution was extracted with Et2O. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give ethyl trans-2-pyridin-4-ylcyclopropanecarboxylate (1.58 g, 52%). LCMS: (FA) ES+ 192.3.

Provenance & Evidence