Hydrochloric Acid → Ethyl 5-(2,2,2-trifluoroethoxy)thiophene-2-carboxylate

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Reaction Steps

To an N,N-dimethylformamide solution (30 mL) of 2,2,2-trifluoroethanol (1.50 g, 15.0 mmol), sodium hydride (655 mg, 15.0 mmol) and ethyl 5-chlorothiophene-2-carboxylate (1.91 g, 10.0 mmol) were added and the resultant mixture was stirred at 65° C. for 6 hours, at room temperature for 15.5 hours, and at 65° C. for 4 hours. After completion of the reaction, water and 1 M hydrochloric acid were added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (464 mg, yield 18%).

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