Tetrahydrofuran → (4,4-Difluorocyclohexyl)methanol

Temperature

0 °C

To a solution of 4,4-difluorocyclohexanecarboxylic acid ethyl ester (150 mg, 0.78 mmol) in diethylether (5 mL) at 0° C. was added a 2 M solution of lithium aluminum hydride in THF (0.39 mL, 0.78 mmol) dropwise. The reaction mixture was stirred at 0° C. for one h. The reaction was quenched with water (1 mL) and 1N NaOH (2 mL) was added, forming a white slurry. The aqueous layer with extracted with EtOAc (2×10 mL) and the organic layers combined, washed with brine, dried with Na2SO4, filtered, and concentrated to yield a clear oil. 1H NMR (CD3OD, 400 MHz) δ (ppm): 3.38 (d, J=6.4 Hz, 2H), 2.05-1.97 (m, 2H), 1.83-1.64 (m, 4H), 1.58-1.50 (m, 1H), 1.29-1.19 (m, 2H).

1. customThe reaction was quenched with water (1 mL) and 1N NaOH (2 mL)
2. additionwas added
3. customforming a white slurry
4. extractionThe aqueous layer with extracted with EtOAc (2×10 mL)
5. washwashed with brine
6. dry with materialdried with Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a clear oil

ORD record

ord-6d969926fe2a46fba87de71a13f1cf2d

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211894B2