Potassium Carbonate → 3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-chloro-phenoxy)-2-methyl-propionic acid

Beteiligte Stoffe

Reaktionsschritte

A mixture of 2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester (0.030 mmol) (see Ex. 26, Part C), toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-yl)ethyl ester (0.030 mmol) (see Ex. 1, Part I) and 325 mesh K2CO3 (0.084 g, 0.60 mmol) in ethanol (2 mL) was heated to reflux for 24 h under N2. Aqueous 5N NaOH (0.5 mL) and additional ethanol (1 mL) was added to the reaction mixture and it was heated at reflux for an additional 2 h. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with aqueous 1 N HCl (5 mL), extracted with water and CH2Cl2 and the organic layer dried by passing it through a Varian Chem Elut 1003 cartridge. The solvent was removed in vacuo to give 3-{4-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-chloro-phenoxy)-2-methyl-propionic acid. 1H NMR (400 MHz, CDCl3) δ 8.05 (d, 2H, J=8.60 Hz), 7.69 (d, 2H, J=8.21 Hz), 7.63 (d, 2H, J=6.65 Hz), 7.48–7.45 (m, 2H), 7.40 (d, 2H, J=7.04 Hz), 7.20–7.15 (m, 4H), 6.82 (d, 3H, J=8.60 Hz), 4.22 (s, 2H), 3.24 (d, 1H, J=13.30 Hz), 3.13–3.07 (m, 3H), 2.43 (s, 3H), 1.25 (s, 3H). MS (ES+) m/z mass calcd for C34H31ClNO5 568.19, found 568.2

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