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

Temperature

0 °C

To an ice-cooled homogeneous solution of 4-(trifluoromethyl)hydrocinnamic acid (9.800 g; 44.918 mmol) in anhydrous THF (250 ml) was added dropwise a solution of 1M BH3.THF (67.4 ml; 67.4 mmol) over 20 min. The resulting homogeneous solution was further stirred at 0° C., under nitrogen, for 1 h, and then at rt for 14 h. The colorless homogeneous reaction mixture was cooled to 0° C., and MeOH (100 ml) was carefully added followed by water (100 ml). MeOH and THF were then removed under vacuum. After extraction with DCM (3×100 ml), the combined organic extracts were washed with brine (100 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=9/1) to give the pure product 3-(4-trifluoromethyl-phenyl)-propan-1-ol as a colorless oil which was further dried under HV (9.180 g; 100%). LC-MS: tR=0.89 min.; [M+H]+: no ionisation.

1. waitat rt for 14 h
2. temperatureThe colorless homogeneous reaction mixture was cooled to 0° C.
3. customMeOH and THF were then removed under vacuum
4. extractionAfter extraction with DCM (3×100 ml)
5. washthe combined organic extracts were washed with brine (100 ml)
6. dry with materialdried over anh. MgSO4
7. filtrationfiltered
8. concentrationconcentrated to dryness under reduced pressure
9. customThe crude was purified by FC (DCM/MeOH=9/1)

ORD record

ord-524c6e18bc9942969d2121b63fd99693

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188082B2