Imidazole → 2-[5-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]-2-thienyl]acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[5-(2-hydroxyethyl)-2-thienyl]acetic acid (1.35 g, 7.26 mmol) and imidazole (1.04 g, 15.25) in N,N-dimethylformamide (18 mL) was added tert-butyldimethylsilyl chloride (2.29 g, 15.25 mmol) over 20 minutes. The resultant solution was stirred at room temperature for one hour. Tetrahydrofuran (18 mL) was then added and reaction solution cooled to 0° C. A solution of potassium carbonate (1.04 g, 7.6 mmol) in water (18 mL) was added and the solution stirred for 20 minutes. The reaction solution was then partitioned between ethyl acetate and brine. The organic phases were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-50% ethyl acetate in iso-hexane to give the title compound as a yellow oil (500 mg, 23%).

Provenance & Evidence