2,2,3,3-Tetrafluoro-1-propanol → HCID 58042434, compound

2,2,3,3-Tetrafluoropropan-1-ol (5.54 g, 41.31 mmol) was added to a suspension of sodium hydride (2.20 g, 55.08 mmol, 60% in mineral oil) in tetrahydrofuran (50 mL) and reaction mixture was stirred for 30 minutes at room temperature. Then a solution of 2-chloro-3-(trifluoromethyl)pyridine (5.00 g, 27.54 mmol) in tetrahydrofuran (50 mL) was added and mixture was heated at 40° C. for 18 hours. The reaction mixture was allowed to cool to room temperature and then quenched slowly with water. The layers were separated and the aqueous layer was further extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in heptane to give the title compound as a oil (3.10 g, 41%).

1. temperaturemixture was heated at 40° C. for 18 hours
2. temperatureto cool to room temperature
3. customquenched slowly with water
4. customThe layers were separated
5. extractionthe aqueous layer was further extracted with ethyl acetate
6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customthe filtrate was evaporated
9. customThe crude product was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in heptane

ORD record

ord-506262224f5a496db97f1ed8297d3cb6

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2