Iodoethane → 2-(Thiophen-3-yl)butanenitrile

Participants

Reaction Steps

A cooled solution of 2-(3-thienyl)acetonitrile (3.144 g, 25.52 mmol) in THF (30 mL) under nitrogen was treated with LHMDS in THF (22.70 g, 25.51 mL of 1 M, 25.50 mmol) dropwise over a period of 20 minutes. The mixture was allowed to stir for 30 minutes and then treated with iodoethane (4.180 g, 2.144 mL, 26.80 mmol) dropwise. The reaction was stirred at RT for a further hour and then quenched by the addition of MeOH and concentrated in vacuo. The residue was diluted with water and extracted with EtOAc (2×). The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (6:1 Petroleum ether/EtOAc) to give the product as an oil (708 mg, 18% Yield). 1H NMR (CDCl3, 400 MHz) δ 1.08 (3H, t), 1.93-2.00 (2H, q), 3.86 (1H, m), 7.03 (1H, m), 7.25 (1H, m), 7.37 (1H, m)

Provenance & Evidence