5-Phenyldipyrromethane → HCID 264043, compound

Exemplified for 1-(4-Methylbenzoyl)-5-phenyldipyrromethane (2a). A solution of EtMgBr (50.0 mL, 50.0 mmol, 1.0 M in THF) was added via syringe to a stirred solution of 1a (4.44 g, 20.0 mmol) in THF (20 mL) under argon. The mixture was stirred for 10 min at room temperature and then cooled to −78° C. A solution of 6a (4.58 g, 20.0 mmol) in THF (20 mL) was added. The mixture was stirred for 10 min at −78° C. Then the cooling bath was removed, the mixture was stirred for 20 min, and then the reaction was quenched with saturated aqueous NH4Cl (150 mL). The mixture was diluted with THF (10 mL), washed with water (100 mL), and then dried (Na2SO4). Removal of solvents and chromatography [silica (6×24 cm), CH2Cl2 (2300 mL)] afforded a golden amorphous solid (5.82 g, 86%): mp 69-70° C.; 1H NMR δ 2.43 (s, 3H), 5.55 (s, 1H), 5.95-6.01 (m, 1H), 6.05-6.09 (m, 1H), 6.14-6.18 (m, 1H), 6.67-6.71 (m, 1H), 6.79-6.82 (m, 1H), 7.20-7.35 (m, 7H), 7.72-7.76 (m, 2H), 8.05-8.22 (brs, 1H), 9.50-9.68 (brs, 1H); Anal. Calcd for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found: C, 80.74; H, 5.74; N, 8.25.