反应详情

THF (70 ml) was added to 1,3-dioxan-2-ylethyltriphenylphosphinebromide (6.80 g, 14.9 mmol), followed by adding to the mixture, potassium-t-butoxide (1.68 g, 14.9 mmol) at 0° C., stirring the mixture at the same temperature for 3 hours, dropwise adding to the reaction solution, a 10 ml THF solution of the above 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethylphenyl)ethyl)cyclohexane (2.7 g, 7.7 mmol), stirring the mixture at the same temperature for one hour, further stirring at room temperature for 3 hours, adding water (50 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, distilling off the solvent, purifying the resulting residue according to column chromatography treatment using heptane/ethyl acetate (3/1) as a developing solvent, on silica gel, distilling off the solvent, hydrogenating the residue (3.2 g) in the presence of a catalyst of 5% Pd/C (0.15 g), in ethanol solvent, filtering off the catalyst distilling off the solvent under reduced pressure, and recrystallizing the residue from heptane/ethanol (5/1), to obtain 4-(4-(1,3-dioxan-2-ylethyl)cyclohexyl)-1-(2-(4-trifluoromethylphenyl)ethyl)cyclohexane (1.46 g, 3.23 mmol). The yield of this product from 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethylphenyl)ethyl)cyclohexane was 42%.

1. additiondropwise adding to the reaction solution
2. stirringfurther stirring at room temperature for 3 hours
3. extractionextracting the resulting product with ethyl acetate
4. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
5. dry with materialdrying over magnesium sulfate
6. distillationdistilling off the solvent
7. custompurifying the resulting residue
8. distillationon silica gel, distilling off the solvent
9. filtrationin ethanol solvent, filtering off the catalyst
10. distillationdistilling off the solvent under reduced pressure
11. customrecrystallizing the residue from heptane/ethanol (5/1)