Tetrahydrofuran → HCID 178509794, compound

Temperature

-20 °C

A mixture of (3-fluoropropyl)triphenylphosphonium bromide (10.0 g, 24.8 millimols) with THF (50 ml) was cooled down to -20° C., followed adding t-BuOK (3.1 g, 27.3 millimols) to the mixture, stirring the resulting mixture for 30 minutes, dropwise adding to the mixture, a THF (60 ml) solution of trans-4-(4-cyanophenyl)cyclohexanecarbaldehyde (5.8 g, 27.3 millimols) so as to keep the temperature at -20° C. or lower, stirring the mixture at the same temperature for 2 hours, adding water (50 ml) to the reaction product after completion of the reaction, extracting the product with ethyl acetate (300 ml), three times washing the resulting organic layer with water, drying it over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and subjecting the residue to silica gel column chromatography (eluent: toluene), to obtain raw 4-(trans-4-(4-fluorobutenyl)cyclohexyl)benzonitrile (5.0 g).

1. additiondropwise adding to the mixture
2. customat -20° C.
3. stirringlower, stirring the mixture at the same temperature for 2 hours
4. customafter completion of the reaction
5. extractionextracting the product with ethyl acetate (300 ml), three times
6. washwashing the resulting organic layer with water
7. dry with materialdrying it over anhydrous magnesium sulfate
8. distillationdistilling off the solvent under reduced pressure

ORD record

ord-21e80bffd2dd4ed097eaf0f4c85fbd68

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05653911