Hydrochloric Acid → Methyl 4-(2,2,3,3,3-pentafluoro-1-hydroxy-1-methylpropyl)benzoate

To a solution of methyl 4-acetylbenzoate (700 mg, 3.85 mmol) in tetrahydrofuran (7.7 mL) were added (pentafluoroethyl)trimethylsilane (1370 mg, 6.93 mmol) and tetrabutylammonium fluoride (tetrahydrofuran solution, 1 mol/L, 5.7 μL, 5.78 mmol) at 0° C., and the mixture was stirred at room temperature overnight. To the solution was added 1 mol/L hydrochloric acid solution, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, filtered through Phase-separator (Varian Inc.), and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→70:30) to give methyl 4-(2,2,3,3,3-pentafluoro-1-hydroxy-1-methylpropyl)benzoate (765 mg, 67%) as a pale yellow viscous material.

1. extractionthe mixture was extracted with ethyl acetate three times
2. filtrationfiltered through Phase-separator (Varian Inc.)
3. concentrationconcentrated under reduced pressure
4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→70:30)

ORD record

ord-b22825a569304dc7b52afb203050201b

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2