(Trifluoromethyl)trimethylsilane → 1-(5-Chloropyridin-2-yl)-2,2,2-trifluoroethan-1-ol

Temperature

0 °C

To a solution of 5-chloropicolinaldehyde (0.505 g, 3.57 mmol) in THF (7 mL) at 0° C. were added (trifluoromethyl)trimethylsilane (0.685 mL, 4.63 mmol) and tetra-N-butylammonium fluoride (1 M in THF, 0.036 mL, 0.036 mmol). The reaction mixture was stirred at 0° C. for 15 min and diluted with water (10 mL) and additional tetra-N-butylammonium fluoride (1 M in THF, 2.0 mL, 2.0 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 30 min. The reaction mixture was diluted with EtOAc, the organic phase was separated and washed with water, brine and dried over MgSO4. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (5% to 20% EtOAc in heptane) to give the title compound (0.643 g, 3.04 mmol, 85% yield) as a yellow oil. MS m/z=211.9 [M+H]+. Calculated for C7H5ClF3NO 211.0.

1. temperatureto warm to room temperature
2. stirringstirred for 30 min
3. customthe organic phase was separated
4. washwashed with water, brine
5. dry with materialdried over MgSO4
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe residue was purified by flash column chromatography on silica gel (5% to 20% EtOAc in heptane)

ORD record

ord-d78d2bebd3b54d87b2b84728be56f744

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2