Acetic Acid → 2-[4-(2-ethyl-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred solution of 2-{[4-(2-hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone (step 1 in EXAMPLE 3, 1.2 g, 4.5 mmol) in dichloromethane (10 mL) was added propionyl chloride (1.0 mL, 11.1 mmol) at ambient temperature. After 1 h, the reaction mixture was partitioned between ethyl acetate (30 mL) and water (10 mL). The aqueous phase was extracted with ethyl acetate (3×30 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. To the residue was added ammonium acetate (7.7 g, 100 mmol) and AcOH (15 mL) and the mixture was heated at 100° C. for 10 h. After cooling, the mixture was diluted with MeOH and basified with 4N NaOH aq. at 0° C. After 30 min, volatile components were removed under reduced pressure. The aqueous phase was extracted with dichloromethane (4×20 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2) to afford 0.32 g (23%) of the title compound as brown amorphous: 1H-NMR (CDCl3)δ1.19 (3H, t, J=7.5 Hz), 2.16 (3H, s), 2.57 (3H, q, J=7.5 Hz), 2.97 (2H, t, J=6.4 Hz), 3.96 (2H, t, J=6.4 Hz), 7.19-7.26 (3H, m), 7.38-7.43 (4H, m), 7.79 (2H, dd, J=7.1, 1.4 Hz).

Herkunft & Nachweise