HCID 11197766, compound → HCID 67354173, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution at −78° C. containing 1.42 g (4.63 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyridine (16) in 20 mL of anhydrous THF were added 5.15 mL (9.27 mmol) of a 1.8 M solution of PhLi in hexane followed by 1.45 g (4.63 mmol) of 9-bromo-1-(benzyloxy)nonane (1). The reaction mixture was stirred under argon atmosphere at −78° C. for 30 min. then the reaction mixture was warmed to room temperature slowly, and the reaction mixture was stirred 30 min. The reaction was quenched with saturated aqueous NaHCO3 and the poured into 150 mL of water. The mixture was then extracted with two portions of 150 mL of ethyl acetate. The combined organic solution was then washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 4:1 gave the expected product as light yellow oil: yield 1.22 g (49%) 1H-NMR (CDCl3) δ 7.54-7.37 (m, 10H), 6.93, (s, 1H), 5.94 (s, 2H), 4.95 (s, 2H), 4.55 (s, 2H), 3.52 (t, 2H, J=6.4), 2.91 (t, 2H, J=8.0) 2.39 (s, 3H), 2.51 (s, 6H), 1.82 (m, 2H), 1.65 (m, 2H), 1.33 (m, 12H); 13C-NMR (CDCl3) δ 155.94, 150.86, 146.89, 142.59, 138.80, 136.92, 128.69, 128.49, 128.38, 127.81, 127.65, 127.49, 121.75, 106.55, 75.30, 72.89, 70.55, 32.21, 29.85, 29.68, 29.63, 29.60, 29.59, 29.57, 29.53, 28.99, 26.27, 16.42, 13.30.

Provenance & Evidence