Ethanol → 4-(2-Fluoropyridin-3-yl)cyclohexanol

Temperature

40 °C

To a 150 mL round bottom flask was added 4-(2-fluoropyridin-3-yl)cyclohex-3-enol (324 mg, 1.677 mmol) followed by Ethanol (14.000 ml):Tetrahydrofuran (2.80 ml) and Palladium on carbon, 10% wt. (32.4 mg, 0.304 mmol). The system was evacuated and backfilled with nitrogen and hydrogen before leaving the reaction suspension exposed to the latter. It was stirred for 16 h at 1 atm. An additional 20% by weight of Pd/C was added before placing the vessel's interior under a hydrogen atmosphere using the same procedure used originally. The reaction was also heated to 40° C. After an additional 2 h, the reaction was complete. The black suspension was cooled to room temperature and filtered over Celite with two ethyl acetate rinses (2×30 mL). The clear filtrate was concentrated under reduced pressure and used without purification.

1. customThe system was evacuated
2. custombefore leaving the reaction suspension
3. waitAfter an additional 2 h
4. temperatureThe black suspension was cooled to room temperature
5. filtrationfiltered over Celite with two ethyl acetate rinses (2×30 mL)
6. concentrationThe clear filtrate was concentrated under reduced pressure
7. customused without purification

ORD record

ord-41475f0bba0044c193491f52370e0c39

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637500B2