2-Fluorophenoxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester → 2-(2-Fluorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester

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Reaction Steps

3-(4-Benzyloxy-phenyl)-2-(2-fluoro-phenoxy)-2-methyl-propionic acid ethyl ester (12.8 g, 31.34 mmol) is dissolved in ethanol (500 mL), treated with 10% palladium on carbon (6.0 g), and stirred under an atmosphere of hydrogen for 90 minutes. The suspension is filtered through celite and concentrated to provide 2-(2-Fluoro-phenoxy)-3-(4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (9.65 g, 97%). The title compound is separated by chiral chromatography (Column OJ, 40% IPA in heptane, 1 mL/mmin, 240 nm UV. 1H NMR (400 MHz, CDCl3): δ 7.13 (d, 2H, J=8.0 Hz), 7.07-7.02 (m, 1H), 6.98-6.88 (m, 3H), 6.74 (d, 2H, J=8.0 Hz), 6.05 (s, 1H), 4.20 (q, 2H, J=6.9 Hz), 3.24, 3.16 (ABq, 2H, J=13.4 Hz), 1.39 (s, 3H), 1.23 (t, 3H, J=6.8 Hz).

Provenance & Evidence