Hydrochloric Acid → 5-(Trifluoromethyl)-3-thiophenemethanol

Temperature

50 °C

To a suspension of lithium borohydride (15.9 g) in tetrahydrofuran (550 ml) was added dropwise a solution of methyl 5-(trifluoromethyl)thiophene-3-carboxylate (55.1 g) in tetrahydrofuran (50 ml) at 0° C., and the obtained mixture was stirred at 50° C. overnight. The reaction mixture was cooled to 0° C., poured into 2 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (37.3 g).

1. temperatureThe reaction mixture was cooled to 0° C.
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-e86be9f922cb40ee920ac6318d440dc9

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199963B2