Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-acrylic acid ethyl ester

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Reaction Steps

A solution of 2-(3-chloro-5-formyl-pyridin-2-yl)-2-methyl-propionitrile (0.58 g, 2.78 mmol) from step 3 above and (carbethoxymethylene)triphenylphosphorane (1.26 g, 3.61 mmol) in dry THF (12 mL) was heated to 55° C. and maintained at this temperature overnight. The solvents were removed and the residue was purified by flash column chromatography (0-20% EtOAc in hexanes) to give the product (0.74 g, 96% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.35 (t, J=7.7 Hz, 3H), 1.87 (s, 6H), 4.29 (q, J=14, 7.7 Hz, 2H), 6.53 (d, J=16 Hz, 1H), 7.65 (d, J=16 Hz, 1H), 7.87 (d, J=2 Hz, 1H), 8.58 (d, J=2 Hz, 1H). ESIMS (MH+): 279.

Provenance & Evidence