Ethyl Acetate → HCID 19815428, compound

Participants

Reaction Steps

To a solution of 4-chloro-2-heptyl-5-(hydroxymethyl)imidazole (5.2 g, 20.7 mmol) in dry DMF (100 mL) was added anhydrous K2CO3 (4.3 g, 31.1 mmol) followed by 4-nitrobenzylbromide (5.4 g, 24.9 mmol). The solution was stirred 3-5 hours at 65°-70°. The reaction mixture was poured into a separatory funnel containing EtOAc and H2O (300 mL each). The aqueous phase was extracted with EtOAc (150 mL) and the combined organic phases were washed three times with H2O (150 mL) before being dried (MgSO4), filtered and concentrated to give 9.0 g brown crude oil. Chromatography (silica gel, 450 g; 1:1 EtOAc/hexanes) gave 1.3 g (17% overall, 35% of theoretical); m.p. 110°-115°. NMR (200 MHz, CDCl3) δ 8.20 (d, 2H, 5 Hz); 7.20 (d, 2H, 5 Hz); 5.35 (s, 2H); 4.45 (s, 2H); 3.10-3.00 (m, 1H); 2.50 (t, 2H, 5 Hz); 1.75-1.50 (m, 2H); 1.40-1.10 (m, 8H); 0.90-0.75 (m, 3H). Mass Spec. 365.

Provenance & Evidence