Imidazole → HCID 53720908, compound

Participants

Reaction Steps

A solution of imidazole (2.32 g, 34.1 mmol), the title compound of Step 10 (5.0 g, 22.7 mmol) and NaHCO3 (6.58 g, 78.3 mmol) in anhydrous EtOH (40 mL) was refluxed overnight in a modification of the procedure of Bach et al, [J. Am. Chem. Soc., 79, 2221-2225 (1957)]. After filtration, the filtrate was concentrated to a yellow oil. The oil was dissolved into a 1.0M KOH solution (10 mL) and was extracted with EtOAc (3×5 mL). The organic layer was washed with a 5% NaHCO3, solution (5 mL), H2O (5 mL), and brine (5 mL) and then was dried over MgSO4. The filtrate was concentrated and purified by medium pressure column chromatography on silica gel [eluting with NH4OH-EtOH-CHCI3 (1:4: 94)] to give the title compound as an oil (1.69 g, 30% yield). The proton spectral data were consistent with the proposed structure.

Provenance & Evidence