Triethylamine → HCID 18319509, compound

Participants

Reaction Steps

A mixture of zinc (69.2 mg, powder) and potassium cyanide (0.12 g) in N,N-dimethylformamide (10.5 ml) was stirred for 10 minutes under nitrogen atmosphere at ambient temperature and thereto was added successively ethyl 2,3-dihydro-9-trifluoromethanesulfonyloxy-1-benzoxepin-4-carboxylate (0.53 g), triethylamine (0.25 ml), and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (0.12 g, complex with dichloromethane (1:1)). The reaction mixture was stirred at 60° C. for 2 hours. Thereto was added a mixture of ethyl acetate and water, basified by aqueous potassium carbonate, and filtered off. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:9) to give a solid of ethyl 9-cyano-2,3-dihydro-1-benzoxepin-4-carboxylate (310 mg).

Provenance & Evidence