Reaction Steps
Compound 16 (2.05 g, 5.2 mmol) was suspended in toluene (100 mL), and refluxed with oxalyl chloride (2.0 mL, 23.2 mmol) for five hours. Volatile components were removed, and the white solid was taken in CH2Cl2 (50 mL) and added dropwise while stirring to a solution containing resorcinol (1.23 g, 11.2 mmol), triethylamine (5.4 mL, 39 mmol), and DMAP (0.06 g, 0.52 mmol). Following stirring at room temperature for 12 hours, the mixture was then refluxed for twenty four hours. The solvent was removed under reduced pressure, and the residue purified by column chromatography (CH2Cl2:EtOH, 10:0.03, and then CH2Cl2:EtOH, 10:0.3). The product was then recrystallized from ethanol. Yield (1.6 g, 64%). 1H NMR: δH (CDCl3; 300 MHz): 0.92 (3 H, t, 3J=6.9 Hz, CH3), 1.23-1.60 (14 H, m, CH2), 1.86 (2 H, m, O—CH2—CH2), 4.07 (2 H, t, 3J=6.5 Hz, O—CH2), 6.15 (1 H, bs, OH), 6.69 (2 H, m, Ar—H), 6.78 (1 H, d, 3J=8.3 Hz, Ar—H), 7.01 (2 H, d, 3J=8.9 Hz, Ar—H), 7.25 (1 H, t, 3J=8.5 Hz, Ar—H), 7.38 (2 H, d, 3J=8.8 Hz, Ar—H), 8.18 (2 H, d,3J=8.9 Hz, Ar—H), 8.27 (2 H, d, 3J=8.8 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 14.5, 23.1, 26.4, 29.5, 29.7, 29.8, 30.0, 32.3, 68.8, 109.8, 113.8, 113.9, 114.9, 121.2, 122.6, 127.2, 130.5, 132.3, 132.9, 152.0, 155.8, 157.4, 164.3, 165.0, 165.3.
