Ethyl cyanoacetate → Ethyl 4-cyanooxane-4-carboxylate

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Reaction Conditions

Reaction Steps

Ethyl cyanoacetate (22.6 g, 0.2 mol) and bis(2-chloroethyl)ether (14 g, 0.1 mol) were added to a suspension of potassium carbonate (70 g, 0.5 mol) in N,N-dimethylformamide (150 ml), and the mixture stirred at 100° C. for 72 hours. The cooled mixture was partitioned between water and diethyl ether (500 ml), the layers separated and the aqueous solution extracted with diethyl ether (3×200 ml). The combined organic solutions were washed with 2N hydrochloric acid (3×100 ml), brine (2×100 ml), dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. This crude product was purified by column chromatography on silica gel using ethyl acetate:cyclohexane (50:50) as eluant, to afford the title compound, 9.3 g.

Provenance & Evidence