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

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%).

1. washThe organic layer was washed with a saturated sodium chloride aqueous solution
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-0969ff32b85f4b6cb94634e3e8c6b40e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403798B2