Sodium hydride → HCID 66751577, compound

Participants

Reaction Steps

To sodium hydride (149 mg, 55% in mineral oil, 3.42 mmol) in tetrahydrofuran (240 ml) was added a solution of (3H-imidazol-4-ylmethyl)-isopropyl-(3-nitro-phenyl)-amine (685 mg, 2.63 mmol) in tetahydrofuran (100 ml) and stirring was continued for 45 min at room temperature. The reaction mixture was cooled with an ice bath and 2-(trimethylsilyl)ethoxymethylchloride (439 mg, 2.63 mmol) was added. After stirring the suspension overnight the reaction was quenched with saturated sodium bicarbonate solution. Tetrahydrofuran was evaporated and the residue was extracted with ethyl acetate twice. The combined organic layers were washed with water, dried over magnesium sulphate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: heptane/ethyl acetate=80:20) to yield a light yellow oil, (0.20 g, 20%); MS (ISP): 391.3 ((M+H)+.).

Provenance & Evidence