Hydrochloric Acid → HCID 67546723, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-chloro-3-hydroxy-2,2-dimethyl-indan-1-one (1.10 g, 5.24 mmol) in THF (50 mL) is added methyl 4-imidazolecarboxylate (CAS#17325-26-7, 1.0 g, 7.85 mmol), followed by triphenylphosphine (2.1 g, 7.85 mmol). The reaction is cooled to 0° C. and di-t-butyl azodicarboxylate (1.8 g, 7.85 mmol) is added. The reaction is permitted to warm to room temperature and stirred for 2 hours. The reaction mixture is then cooled to 0° C., quenched with 4 N HCl in dioxane (5 mL, 20 mmol) and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCl. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The organic layers are combined, dried over Na2SO4, filtered concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:1) to furnish 3-(4-chloro-2,2-dimethyl-3-oxo-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 319.0 (M+H)+

Provenance & Evidence