Borane;tetrahydrofuran → 2-[4-(Trifluoromethoxy)phenyl]ethanol

To a stirred solution of 1.0 g (4.54 mmol) of 4-(trifluoromethoxy)-phenylacetic acid in 15 mL of anhydrous THF at 0° C. was added dropwise 9 mL (9.08 mmol) of 1 M BH3THF and the reaction allowed to warm to RT over 16 h. The mixture was cooled back down to 0° C. and the reaction quenched with 15 mL of water/acetic acid/THF (1:1:3). After warming to RT, the solvent was removed in vacuo, the residue diluted with water, and the solution extracted with EtOAc. The layers were separated, the organics washed with NaHCO3, the layers separated, the organics dried (MgSO4), and the solvent removed in vacuo. The residue was purified by silica gel chromatography using EtOAc/hexane (1:1) as eluent to give 540 mg (57% yield) of the title compound: TLC (EtOAc/hexane (1:1)): Rf=0.43.

1. temperatureThe mixture was cooled back down to 0° C.
2. customthe reaction quenched with 15 mL of water/acetic acid/THF (1:1:3)
3. temperatureAfter warming to RT
4. customthe solvent was removed in vacuo
5. additionthe residue diluted with water
6. extractionthe solution extracted with EtOAc
7. customThe layers were separated
8. washthe organics washed with NaHCO3
9. customthe layers separated
10. dry with materialthe organics dried (MgSO4)
11. customthe solvent removed in vacuo
12. customThe residue was purified by silica gel chromatography

ORD record

ord-ab3a24bd2f3e46689290f01002c2e003

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06294580B1