Methanol → 3-(4-(Trifluoromethyl)phenyl)propan-1-ol

Temperature

0 °C

In an inert atmosphere, 3-(4-Trifluoromethyl-phenyl)-propionic acid (10 g, 45.8 mmol) was dissolved in anhydrous THF (250 ml) and cooled to 0° C. followed by the addition of a 1 M solution of borane in THF (69 ml, 69 mmol). Stirring was continued at 0° C. for 1 h and 16 h at rt followed by slow addition of methanol (100 ml) and water (100 ml). The organic solvents were evaporated under reduced pressure. The remaining water phase was extracted with DCM (3×100 ml) and the combined organic layers were washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silicagel, DCM/methanol=9/1 to give 9.25 g (99%) of 3-(4-Trifluoromethyl-phenyl)-propan-1-ol. LC-MS: tR=0.89 min; [M+H]+=no ionisation.

1. customThe organic solvents were evaporated under reduced pressure
2. extractionThe remaining water phase was extracted with DCM (3×100 ml)
3. washthe combined organic layers were washed with brine (100 ml)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by flash chromatography (silicagel, DCM/methanol=9/1

ORD record

ord-09dc222dbf814b7c859600bb67b899e8

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834028B2