Ethyl Acetate → Ethyl 2-(4-cyanopyridin-3-YL)acetate

Participants

Reaction Steps

KCN (2.64 g, 31.44 mmol) in water (8 mL) was added drop wise over a period of 20 minutes to a solution of 3-(2-ethoxy-2-oxoethyl)pyridine-1-oxide ethyl iodide (I-67b: 5.3 g, 15.72 mmol) in ethanol-water (7:3 ratio, 30 mL) at 50° C. and heating was further continued for another 30 minutes. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was quenched using ice and extracted using DCM. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 2.4 g of the product.

Provenance & Evidence