Acetic Acid → (E)-2-cyano-oct-2-enoic acid methyl ester

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Reaction Steps

Hexanal (6.06 ml, 50 mmol) and piperidine (0.16 ml) were added to a solution of mehtylcyano acetate (4.4 ml, 49 mmol) in acetic acid (6.8 ml). The solution was stirred for 14 h at ambient temperature and poured onto ice water/dichloromethane 1/1. The layers were separated and the aqueous layer was extracted two times with dichloromethane. The combined extracts were washed with ice water, dried over sodium sulfate and the solvent was removed under reduced pressure to yield (E)-2-cyano-oct-2-enoic acid methyl ester as yellow oil (9.66 g, 53 mmol; quant.) which was used in the next step without further purification. MS: m/e=199.1 [M+NH4+].

Provenance & Evidence