2,2,2-Trifluoroacetaldehyde hydrate → 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)but-2-enoic acid ethyl ester

Temperature

100 °C

To a solution of 4,4,4-trifluoro-2-(triphenyl-λ5-phosphanylidene)-butyric acid ethyl ester (2.0 g, 4.65 mmol) in THF (5 mL) was added 1 mL of trifluoroacetaldehyde hydrate (tech.). The mixture was sealed in a pressure tube and heated at 100° C. for 3.5 h. After cooling to 23° C., the reaction mixture was eluted through a pad of silica gel (100 g) and Na2SO4 with Et2O (100 mL) to remove the by-products triphenylphosphine oxide and water. The eluent was distilled to remove Et2O and to afford the product as a colorless liquid (1.0 g, 86%).

1. customThe mixture was sealed in a pressure tube
2. temperatureAfter cooling to 23° C.
3. washthe reaction mixture was eluted through a pad of silica gel (100 g) and Na2SO4 with Et2O (100 mL)
4. customto remove the by-products triphenylphosphine oxide and water
5. distillationThe eluent was distilled
6. customto remove Et2O

ORD record

ord-e258429c95244f978a203d3c7c534238

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547725B2