Potassium Cyanide → Methyl 5-(cyanomethyl)thiophene-3-carboxylate

Participants

Reaction Steps

A solution of potassium cyanide (3.2 g, 48.5 mmol) in DMF (25 mL) is treated with 5-chloromethyl-thiophene-3-carboxylic acid methyl ester (4.4 g, 23.1 mmol) in DMF (30 mL). After stirring for 14 h at room temperature the mixture is warmed to 50° C. for 0.5 h. After cooling, the solution is diluted with saturated aq NaCl and extracted with CHCl3 (3×). The combined organic layers are dried over MgSO4, filtered and concentrated in vacuo to give 5-cyanomethyl-thiophene-3-carboxylic acid methyl ester (4.4 g, 100%). 1H NMR (CDCl3, 300 MHz) δ 8.00 (s, 1 H), 7.44 (s, 1 H), 3.90 (s, 2 H), 3.84 (s, 3 H).

Provenance & Evidence