Tetrahydrofuran → 1-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethan-1-ol

Temperature

0 °C

6-Chloronicotinaldehyde (500 mg, 3.53 mmol) was added to tetrahydrofuran (23 mL) and cooled to 0° C. Trimethyl(trifluoromethyl)silane (0.66 mL, 4.24 mmol) was added followed by 1 M tetra-n-butylammonium fluoride in tetrahydrofuran (4.24 mL, 4.24 mmol). The reaction mixture was allowed to warm to room temperature over 1 hour. The reaction was then diluted with water and brine and extracted with ethyl acetate three times. The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated in vacuo. The concentrated material was purified via silica gel chromatography (0-40% ethyl acetate in hexanes) to afford the title compound.

1. temperatureto warm to room temperature over 1 hour
2. extractionextracted with ethyl acetate three times
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe concentrated material was purified via silica gel chromatography (0-40% ethyl acetate in hexanes)

ORD record

ord-880a335049c14a5d99615e628f554029

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2