HCID 18956332, compound → HCID 18956329, compound

Participants

Reaction Conditions

Reaction Steps

Part B. A solution of the ester obtained in Part A above (9.54 g, 33.1 mmol) in tetrahydrofuran (30 mL) was added to a solution of lithium aluminum hydride (80 mmol) in tetrahydrofuran (80 mL) at 0° C. The mixture was heated to reflux overnight, then cooled back to 0° C. and quenched by the careful sequential addition of water (3 mL), then aqueous sodium hydroxide solution (10 mL of 15%), then water (10 mL). The mixture was filtered through celite with copius tetrahydrofuran washing, and the liquid was dried over anhydrous potassium carbonate, filtered and evaporated. The residual oil was separated by flash chromatography (ethyl acetate) to afford the product, 1-(5-hydroxypentyl)-2-(1-methylethyl)-1H-benzimidazole (6.82 g, 27.7 mmol, 84%) as an oil. 1H NMR (CDCl3) : 7.78-7.70 (1H, m); 7.32-7.22 (3H, m); 4.90 (1H, br d, J=2.2 Hz); 4.12 (2H, t, J=7.5 Hz); 3.64 (2H, t, J=6.0 Hz); 3.18 (1H, m, J=6.6 Hz); 1.93-1.45 (6H, m); 1.44 (6H, d, J=6.6 Hz).

Provenance & Evidence