Lithium diisopropylamide → HCID 19430447, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-fluoro-4-iodobenzyl)-5-acetyl-4-ethyl-2-propyl- 1H-imidazole (5.52 g, 13.3 mmol) was dissolved in 50 mL of THF. The mixture was cooled at 0° C. under N2 and lithium diisopropylamide (7.3 mL of 2M in THF, 14.6 mmol) was added. After stirred at 0° C. for 15 minutes, a solution of o-phenoxybenzyl iodide (5.22 g, 16.8 mmol) in THF (15 mL) was added. The reaction mixture was warmed up to room temperature and stirred for 2 h. The mixture was partitioned between EtOAc and H2O. The two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic solution was washed with brine, dried over MgSO4. It was concentrated and chromatographed on silica gel with 10-50% EtOAc/hexane to yield 2.35 g of the desired product. MS m/e 597.2, [M+H]+ ; IR (KBr): 1646 cm-1 for CO; 1H NMR (300 MHz, CDCl3): δ 0.95 (t, 3H, CH3), 1.22 (t, 3H, CH3), 1.65 (m, 2H, CH2), 2.57 (m, 2H, CH2), 2.82 (q, 2H, CH2), 2.98 (m, 2H, CH2), 3.10 (m, 2H, CH2) 5.42 (s, 2H, CH2Ar), 6.22 (t, 1H, ArH), 6.82 (d, 1H, ArH), 6.90 (d, 2H, ArH), 7.02 (m, 2H, ArH), 7.18 (d, 1H, ArH), 7.22 (m, 2H, ArH), 7.30 (m, 2H, ArH), 7.40 (d, 1H, ArH). ##STR66##

Provenance & Evidence