Reaction Steps
To a stirred solution at −78° C. containing 906 mg (2.95 mmol) of 3-(benzyloxy)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-2,4-dimethylpyridine in 20 mL of anh. THF were added 789 mg (2.95 mmol) of 1-bromo-9-(methoxymethoxy)nonane followed by 1.99 mL (3.54 mmol) of a 1.80 M solution of PhLi in hexane. The reaction mixture was stirred at −78° C. for 30 min. then the reaction mixture was warmed to 23° C. slowly, and the reaction mixture was stirred 30 min. The reaction was quenched with satd aq ammonium chloride and then poured into 80 mL of water. The mixture was then extracted with two 80-mL portions of ethyl acetate. The combined organic layer was then washed with a 100-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as a light yellow oil: yield 877 mg (60%); silica gel TLC Rf 0.3 (9:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.18-1.22 (br m, 12H), 1.50 (quint, 2H, J=6.8 Hz), 1.65 (m, 2H), 2.06 (s, 6H), 2.26 (s, 3H), 2.75 (dd, 2H, J=7.6, 7.6 Hz), 3.28 (s, 3H), 3.43 (t, 2H, J=6.8 Hz), 4.53 (s, 2H), 4.82 (s, 2H), 5.78 (s, 2H), 6.79, (s, 1H) and 7.29-7.40 (m, 5H); 13C NMR (CDCl3) δ 13.30, 13.30, 16.35, 26.19, 28.92, 29.40, 29.48, 29.50, 29.55, 29.61, 29.73, 32.13, 55.05, 67.86, 75.24, 96.36, 106.40, 106.40, 121.68, 121.68, 127.73, 127.90, 127.90, 128.89, 128.89, 138.83, 141.97, 141.97, 146.80, 150.76 and 155.88; mass spectrum (APCI), m/z 493.3426 (M+H)+ (C31H45N2O3 requires 493.3430).
