Potassium Carbonate → 2-(4-{2-[5-Methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-benzyl)-2-phenoxy-hexanoic acid

Participants

Reaction Steps

A mixture of 2-(4-hydroxybenzyl)-2-phenoxyhexanoic acid ethyl ester (0.030 mmol) (see Ex 61, Part C), toluene-4-sulfonic acid 2-[5-methyl-2-(3-thiophen-2-ylphenyl)oxazol-4-yl]ethyl ester (0.030 mmol) (see Ex. 5, Part B) 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 2-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-benzyl)-2-phenoxy-hexanoic acid. 1H NMR (400 MHz, CDCl3) δ 8.15–8.12 (m, 1H), 7.79 (d, 1H, J=7.43 Hz), 7.57 (d, 1H, J=7.82 Hz), 7.37–7.32 (m, 2H), 7.24–7.18 (m, 3H), 7.01 (dd, 1H, J=5.08 Hz, J=3.52 Hz), 6.99–6.87 (m, 5H), 6.68 (d, 2H, J=8.99 Hz), 4.10 (t, 2H, J=6.65 Hz), 3.21 (s, 2H), 2.91 (t, 2H, J=6.65 Hz), 2.31 (s, 3H), 2.02–1.88 (m, 2H), 1.34–1.08 (m, 4H), 0.71 (t, 3H, J=7.04 Hz); MS (ES+) calcd for C35H36NO5S: Found m/e 582.2 (M+1, 100%).

Provenance & Evidence