(Trimethylsilyl)imidazole → HCID 178437186, compound

Participants

Reaction Conditions

Reaction Steps

Titanium tetrachloride (3.28 ml, 29.9 mmol) was added to anhydrous chloroform (25 mL) at 0° C. 1-Trimethylsilanyl-1H-imidazole (4.38 ml, 29.9 mmol) in chloroform (25 ml) was added slowly (6 to 7 m) to the TiCl4 solution. The resulting orange solid mixture was stirred at 0° C. for 30 m followed by the addition of (13) (3.53 g, 15.0 mmol) in chloroform (15 mL). The mixture was warmed to room temperature and stirred overnight. The mixture was quenched with water (60 mL). The two layers were separated and the organic layer was extracted twice with water (40 mL). The pooled aqueous layer was neutralized with 4 M NaOH to pH>8. The basic aqueous layer was to extracted with dichloromethane numerous times. The pooled organic layers were washed with brine once, and dried over magnesium sulfate. The mixture was filtered, and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane to give 8-(1-(1H-imidazol-4-yl)ethyl)quinoline (14) as an off white solid (1.61 g, 7.22 mmol, 48% yield.)

Provenance & Evidence