HCID 56655506, compound → HCID 68046642, compound

Participants

Reaction Steps

A solution of 5-(3-acetylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-17, 170 mg, 0.51 mmol) in anhydrous THF (5 ml) was cooled to −78 deg C. and treated with Phenyl magnesium chloride (1.8 M in THF, 365 μL, 0.66 mmol, 1.3 eq). The reaction mixture was warmed to 0 deg C. and stirred for 1 h. The reaction was only ˜30% complete, so more of the Grignard reagent (1.8 M in THF, 365 μL, 0.66 mmol, 1.3 eq) was added at 0 deg C. and the reaction was maintained there for 30 min. The completed reaction was partitioned between EtOAc (50 ml) and water (55 ml) and the cloudy, white precipitate present which was removed via filtration. The filtrate was separated in a separatory funnel and the aqueous layer was re-extracted with EtOAc (50 ml). The combined organic layers were dried over Na2SO4, concentrated, then purified via flash column chromatography (SiO2: 100% Hex to 50:50 Hex/EtOAc), affording the title compound, 1-(2,2-dimethylpropyl)-5-[3-(1-hydroxy-1-phenylethyl)phenyl]-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (10-1) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 7.48-7.45 (m, 3H), 7.40-7.31 (m, 4H), 7.27-7.24 (m, 2H), 7.12 (s, 1H), 7.05 (d, 1H, J=8.15 Hz), 3.67 (s, 2H), 3.45 (s, 3H), 2.02 (s, 3H), 1.05 (s, 9H). LRMS m/z: Calc'd for C27H30N2O2(M+H) 415.2, found 415.5.

Provenance & Evidence