Water → (2-(Trifluoromethyl)-1,3-thiazol-5-yl)methanol

Temperature

0 °C

To a suspension of lithium aluminum hydride (2.17 g, 57.1 mmol) in tetrahydrofuran (80 ml) was dropwise added a solution of ethyl 2-(trifluoromethyl)-1,3-thiazole-5-carboxylate (8.579 g, 38.10 mmol) in tetrahydrofuran (40 ml) under ice-cooling and the mixture was stirred at 0° C. 1 hr. The reaction solution was ice-cooled and water (2 ml), 15% aqueous sodium hydroxide solution (2 ml) and water (5 ml) were dropwise added successively to decompose excess lithium aluminum hydride. The mixture was stirred at room temperature as it was for 2 hrs. The resulting precipitate was removed by filtration and the precipitate was washed with ethyl acetate. The solvent of the collected filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−1/1) to give the objective substance.

1. temperaturecooling
2. custom1 hr
3. temperaturecooled
4. stirringThe mixture was stirred at room temperature as it
5. customThe resulting precipitate was removed by filtration
6. washthe precipitate was washed with ethyl acetate
7. customThe solvent of the collected filtrate was evaporated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−1/1)
9. customto give the objective substance

ORD record

ord-bc65fcba86a64cfdbd907f1a3373e014

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2