Reaction Steps
To a solution of oleyl bromide (1.8 g, 5.4 mmol) in cyclohexanone (20 ml) was added protocatachualdehyde (0.341 g, 2.5 mmol), potassium carbonate (1.02 g, 7.4 mmol) and potassium iodide (0.05 g, 0.3 mmol). The suspension was stirred at 100° C. for 18 hours under nitrogen. Due to the light sensitivity of the oleyl bromide the flask was covered in aluminum foil. TLC (10% MeOH/CHCl3) showed the reaction was complete. The hot reaction mixture was filtered to remove some of the particulates and the solvent was removed in vacuo. The residue was dissolved in CHCl3 (100 mL) and washed with water (2×75 mL). The CHCl3 layer was dried over anhydrous sodium sulphate, filtered and the solvent removed in vacuo to give a dark yellow oil. The oily residue was purified by flash column chromatography (5% EtAc/hexane) to yield the product 8a as a white solid (1.08 g, 69%), Rf=0.3 (5% EtAc/hexane). 1H NMR (CDCl3) d 9.80 (s, 1H, CHO), 7.37 (m, 2H, phenyl), 6.93 (d, 1H, phenyl), 5.33 (t, 4H, olefinic), 4.06 (t, 2H, OCH2), 4.04 (t, 2H, OCH2), 2.01 (m, 8H, CH2C═C), 1.85 (m, 4H, CH2CH2O), 1.50-1.18 (m, 44H, 22×CH2), 0.88 (t, 6H, CH3); 13C NMR (CDCl3) d 191.00, 155.34, 149.95, 130.14, 130.12, 129.97, 126.79, 111.89, 111.04, 69.36, 32.29, 30.16, 29.92, 29.90, 29.88, 29.72, 29.64, 29.62, 29.44, 29.36, 27.60, 26.37, 26.34, 23.09, 14.53; HRMS (FAB): theory for C43H75O3 (M+1), 639.5716; found (M+1), 639.5755. Anal. (C43H74O3): C, H.
