Water → 2,2-Difluoro-4-phenylbutan-1-ol

To a cooled solution of Intermediate 1 (1.0 g, 4.45 mmol) in tetrahydrofuran (15 mL) was added lithium aluminum hydride (0.22 g, 5.78 mmol). The mixture was stirred at room temperature overnight. To the crude reaction was added water (0.3 mL), 4N sodium hydroxide (0.3 ml) and water (0.9 mL). The resulting solid was filtered through Celite and the solvent removed under reduced pressure. The residue was diluted with methylene chloride (20 mL) and washed with water (10 mL), 2N hydrochloric acid (2×10 mL) and water (10 mL), dried (Na2SO4), and concentrated. The title compound was obtained as brown oil (0.6 g, 72%).

1. customTo the crude reaction
2. filtrationThe resulting solid was filtered through Celite
3. customthe solvent removed under reduced pressure
4. additionThe residue was diluted with methylene chloride (20 mL)
5. washwashed with water (10 mL), 2N hydrochloric acid (2×10 mL) and water (10 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated

ORD record

ord-624a73789cec4f3a8b325059abbb2ac3

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420669B2