Tetrahydrofuran → HCID 21192136, Verbindung

Temperatur

-50 °C

THF (60 ml) was added to 3-fluoropropyltriphenylphosphinebromide (10.3 g, 25.5 mmol) prepared at the second step of Example 1, followed by cooling the mixture down to -50° C. in nitrogen atmosphere, adding to the mixture, a 40 ml THF solution of potassium-t-butoxide (2.86 g, 25.5 mmol), stirring the mixture at the same temperature for 3 hours, dropwise adding to the reaction solution, a 100 ml THF solution of 4-(3,5-difluorophenyl)cyclohexanone (43.8 g, 20.8 mmol) prepared at the first step, stirring the mixture at the same temperature for one hour, stirring at room temperature for 3 hours, adding water (200 ml) to the reaction solution, extracting the resulting product with ethyl acetate, washing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, purifying an yellow solution obtained by distilling off the solvent, according to column chromatography treatment using toluene as a developing solvent, on silica gel, hydrogenating the resulting cyclohexylidene derivative using a catalyst of Pd/C, in ethanol, filtering off the catalyst after the reaction, distilling off ethanol under reduced pressure and recrystallizing the resulting product using a mixed solvent of heptane with ethanol, to obtain 4-(3,5-difluorophenyl)-1-(3-fluoropropyl)cyclohexane (1.50 g, 6.14 mmol). Yield: 29.5%.

1. customprepared at the second step of Example 1
2. additionadding to the mixture
3. additiondropwise adding to the reaction solution
4. stirringstirring at room temperature for 3 hours
5. extractionextracting the resulting product with ethyl acetate
6. washwashing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water
7. dry with materialdrying over magnesium sulfate
8. custompurifying an yellow solution
9. customobtained
10. distillationby distilling off the solvent
11. filtrationin ethanol, filtering off the catalyst
12. customafter the reaction
13. distillationdistilling off ethanol under reduced pressure
14. customrecrystallizing the resulting product

ORD-Eintrag

ord-a17996756e2e4a26b8646f7a6502b0a4

Quelldatensatz

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05702641