Imidazole → 5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide

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Reaction Steps

5-Hydroxy-3-(4-trifluoromethylphenyl)pentanoic acid amide (350 mg) was dissolved in dimethylformamide (13 mL), and imidazole (365 mg) and tert-butyldiphenylsilyl chloride (697 μL) were added at room temperature. After stirring for one hour, the reaction solution was partitioned with ethyl acetate and water. The organic layer was washed with water (twice), 1 N hydrochloric acid and brine. After drying over magnesium sulfate, concentration under reduced pressure and purification by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 90%) gave the title compound (680 mg).

Provenance & Evidence