Methanol → 2-Cyano-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}-acrylic acid

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Reaction Steps

2-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester (described in Example 6) (0.201 g; 0.483 mmole), lithium hydroxide (0.04 g; 1.67 mmole), methanol (2.3 ml) and water (2.3 ml) was stirred at 40° C. for 23 hours. More water was added, methanol was removed by evaporation in vacuo and the mixture was acidified using potassium hydrogen sulfate. The mixture was extracted with ethyl acetate and the organic phase was dried (sodium sulfate), filtered and evaporated in vacuo. The crude products were purified on preparative HPLC using acetonitrile (gradient 30-60%): ammonium acetate (0.1 M). The fractions were acidified with potassium hydrogen sulfate and then extracted with ethyl acetate. The organic phases were combined and evaporated in vacuo to give 7 mg of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]-phenyl}acrylic acid and 21,8 mg of 2-cyano-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}-acrylic acid.

Provenance & Evidence