Reaction Steps
Phenol 25 (0.656 g., 2.00 mmol, 1 equiv.; from Example 18) is dissolved in 15 mL of methyl isobutyl ketone. 4-[1-Adamantyl]-3-methoxybenzyl iodide (18b) (0.766 g., 2.00 mmol, 1 equiv.) and potassium carbonate (1.00 g., 7.2 mmol, 3.6 equiv.) are added and the mixture is heated to reflux for 5 hours. The solvents are evaporated and the residue is dissolved in methylene chloride. This solution is washed with water and brine, then dried (MgSO4), and concentrated. The crude material is chromatographed on silica gel using 50% CH2Cl2 /hexane to afford 3'-carboethoxy-2-[4-(1-adamantyl)-3-methoxyphenyl]methoxy-[1,1'-biphenyl]-6-acetic acid, ethyl ester (29d) (0.725 g., 1.24 mmol, 62%): 1H NMR (300 MHz, CDCl3) δ 8.06 (dd, J=2, 8 Hz, 1H, ArH), 7.98 (s, 1H, ArH), 7.50-7.47 (m, 2H, ArH), 7.33-6.97 (m, 4H, ArH), 6.69 (dd, J=2, 8 Hz, 1H, ArH), 6.57 (d, J=2 Hz, 1H, ArH), 4.97 (s, 2H, ArCH2O), 4.38 (q, J=7 Hz, 2H, CO2CH2), 4.03 (q, J=7 Hz, 2H, CO2CH2), 3.59 (s, 3H, CH3O), 3.41 (s, 2H, ArCH2CO2), 2.03 (s, 9H, adamantyl), 1.75 (s, 6H, adamantyl), 1.40 (t, J=7 Hz, 3H, CO2CH2CH3), 1.16 J=7 Hz, 3 Hz, CO2CH2CH3); 13C NMR (75 MHz, CDCl3) δ 171.48 (C=O), 166.54 (C=O), 158.84, 156.13, 137.62, 137.33, 135.74, 134.91, 134.21, 131.31, 131.05, 130.44, 128.82, 128.33, 128.14, 126.27, 122.82, 118.09, 111.49, 109.54, 69.75, 60.97, 60.77, 54.82, 40.55, 39.23, 37.13, 36.80, 29.09, 14.38, 14.12.
