Hydrochloric Acid → HCID 69491077, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride, as a 60% mineral oil dispersion (240 mg, 6 mmol) was introduced into a dry round bottomed flask and dry N,N-dimethylformamide (12 ml) was added thereto. The flask was stoppered with a serum cap and flushed with argon. A solution of ethyl cyanoacetate (679 mg, 6 mmol) in N,N-dimethylformamide (3 ml) was added dropwise to the stirred slurry and the reaction was stirred for 10 minutes after the addition was complete. 2-Ethyl iodobenzene was then added in one portion, followed by copper (I) iodide (1143 mg, 6 mmol). The mixture was heated at 95° C. for 4 h, then cooled to 0° C. and poured into 1 N hydrochloric acid (100 ml). Diethyl ether was added; the aqueous layer was removed and extracted again with 3×100 ml of diethyl ether. The ethereal extracts were combined, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The oily residue was purified by flash chromatography using hexane:ethyl acetate: dichlorometane 8:1:1 as eluent, obtaining 326 mg of ethyl cyano(2-ethylphenyl) acetic acid ethyl ester as a colourless oil. Yield 50%.

Provenance & Evidence