HCID 19430487, compound → HCID 19430452, compound

Participants

Reaction Steps

To a solution of 1-(2-fluoro-4-iodobenzyl)-4-ethyl-2-propyl-1H-imidazole-5-carboxaldehyde (16.52 g, 41.3 mmol) in THF (100 mL) was added methylmagnesium bromide (44.0 mL of 1.4/M in toluene/THF, 61.6 mmol) over 30 minutes. The reaction mixture was stirred at room temperature for 1.5 h. It was then quenched with 100 mL of 1N aqueous HCl. The mixture was extracted with CH2Cl2, the organic solution was washed with H2O and brine, dried over MgSO4, and concentrated to a yellow oil (16.87 g). The yellow oil was dissolved in 400 mL of CH2Cl2, and Manganese(IV) oxide (70.50 g, 811 mmol) was added. The mixture was refluxed under N2 overnight. The mixture was cooled. It was then filtered through celite and washed with CH2Cl2. The CH2Cl2 solution was concentrated and chromatographed on silica gel with 50% EtOAc/hexane and 10% MeOH/CH2Cl2 to give 4.70 g of the desired product and 6.87 g of the alcohol. MS m/e 415.0, [M+H]+ ; 1H NMR (300 MHz, CDCl3): δ 0.98 (t, 3H, CH3), 1.35 (t, 3H, CH3), 1.68 (m, 2H, CH2), 2.42 (s, 3H, CH3) 2.58 (m, 2H, CH2), 2.92 (q, 2H, CH2), 5.45 (s, 2H, CH2Ar), 6.28 (t, 1H, ArH), 7.35 (d, 1H, ArH), 7.42 (d, 1H, ArH). ##STR63##

Provenance & Evidence