Reaction Steps
Potassium carbonate (0.165 g, 1.2 mmol) was added to a solution of 1-[2-benzyloxy-4-(methoxymethyloxy)phenyl]-2-iodo-ethanone (0.412 g, 1 mmol) and 4-benzyloxy-salicylalchohol (0.254 g, 1.1 mmol) in 10 mL of acetone and the mixture refluxed for 10 hours. After completion of the reaction (TLC), the solvent was evaporated and the residue extracted with EtOAc:water (2×20 mL:20 mL). The organic layers were combined, dried over sodium sulfate and evaporated. The residue was chromatographed over silica using hexanes:EtOAc (2:1). The organic fractions were evaporated to provide 0.371 g (72%) of white solid: mp 115-118° C.; TLC Rf0.16 in hexanes:EtOAc (2:1); 1H NMR (600 MHz, CDCl3) δ 7.88-7.86 (d, 1H, J=9 Hz, Ar—H5), 7.64-7.25 (m. 10H, 2×C6H5), 7.21-7.20 (d, 1H, J=8.4 Hz, Ar—H6′), 6.92 (d, 1H, J=2.4 Hz, Ar—H8), 6.78-6.76 (dd, 1H, 2J=9 Hz, 3J=2.4 Hz, Ar—H6), 6.56-6.54 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5′), 6.26-6.25 (d, 1H, J=2.4 Hz, Ar—H3′), 5.30 (s, 4H, PhCH2), 5.21 (s, 2H, O—CH2—O), 4.98 (s, 2H, H-2), 4.57-4.56 (d, 2H, J=6 Hz, CH2OH), 4.13-4.11 (t, 1H, CH2OH), 3.44 (s, 3H, OCH3); 13C NMR (100 MHz, CDCl3) δ 194.6, 164.4, 162.2, 160.7, 158.6, 138.9, 137.6, 133.6, 130.2, 129.9, 129.8, 129.2, 125.1, 120.4, 110, 106.8, 102.5, 101.7, 95.6, 75.3, 72.4, 71.2, 61.5, 56.9; analysis calcd. for C31H30O7. C, 72.36; H, 5.88. found: C, 72.1; H, 5.85.
