Methyl iodide → 2-Methyl-2-(thiophen-3-yl)butanenitrile

Participants

Reaction Steps

A cooled solution of 2-(thiophen-3-yl)butanenitrile (708 mg, 4.682 mmol) in THF (15 mL) under nitrogen was treated with LHMDS in THF (4.375 g, 4.916 mL of 1 M, 4.916 mmol) dropwise. After 1 hour the reaction was treated with iodomethane (731.0 mg, 320.6 μL, 5.150 mmol) and then allowed to warm to RT. After 2.5 hours the reaction was quenched with MeOH and then concentrated in vacuo. The mixture was diluted with EtOAc/water and the two layers separated. The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (5:1 Petroleum ether/EtOAc) to give the product as a colourless oil (693 mg, 90% Yield).

Provenance & Evidence