Methanol → Benzenepropanol, 3-(trifluoromethyl)-

Temperature

0 °C

3-(3-Trifluoromethyl-phenyl)-propionic acid (12.4 g, 57 mmol) was dissolved in THF (160 ml) in an inert atmosphere and cooled to 0° C. followed by slow addition of borane in THF (85 ml, 85 mmol). Stirring was continued at 0° C. for 1 h and at rt for 24 h. The mixture was cooled to 0° C. and methanol (100 ml) and water (100 ml) was carefully added. The organic solvents were removed under reduced pressure. The remaining aqueous layer was extracted with DCM (3×100 ml). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silicagel, DCM/methanol=9/1) to give 10.97 g (94%) of 3-(3-trifluoromethyl-phenyl)-propan-1-ol. LC-MS: tR=0.87 min; [M+H]+=no ionisation.

1. temperatureThe mixture was cooled to 0° C.
2. customThe organic solvents were removed under reduced pressure
3. extractionThe remaining aqueous layer was extracted with DCM (3×100 ml)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by flash chromatography (silicagel, DCM/methanol=9/1)

ORD record

ord-634ff4f1b8c84fa8a689a926ec529190

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834028B2