Cesium carbonate → 3-{3-[3-(Biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Participants

Reaction Steps

A mixture of 3-(3-Hydroxyphenyl)-2-methoxy-propionic acid methyl ester (1 eq) from Step D, Cesium Carbonate (3 eq) and 4-(3-bromopropoxy)biphenyl (1 eq) in DMF and in a 10 mL tube was shaked in an orbital agitator over a weekend. The mixture was filtered through a hydrofobic syringer and evaporated in a speed-vac apparatus. Then diluted with NaOH 1N-Ethanol and stirred overnight. Then HCl 3N was added and the reaction mixture was concentrated to remove the ethanol in vacuo, reconstituted in dichloromethane and filtered through a hydrofobic syringe. The organic layer was evaporated to give the title compound. MS (ES) for C25H26O5 [M+NH4]+: 424.2, [M+Na]+: 429.2. 1H-NMR (CDCl3, 200.15 MHz): 7.57–7.17 (m, 9H), 6.98 (dd, 2H, J=6.7, 1.9), 6.84–6.81 (m, 3H), 4.19 (dd, 4H, J=14.0, 6.4), 4.03 (dd, 1H, J=7.3, 4.3), 3.40 (s, 3H), 3.13 (dd, 1H, J=14.2, 4.6), 2.98 (dd, 1H, J=14.0, 7.5), 2.28 (qui, 2H, J=5.9)ppm.

Provenance & Evidence