反应详情

温度

-30 °C

43.01 g (89 mmol) of (3,4-difluorophenyl) ethyltriphenylphosphonium bromide were charged into a 300 ml three-necked flask in a nitrogen atomosphere and dried, and 74 ml of THF were added. The mixture was cooled to −30° C, a solution of 9.99 g (89 mmol) of potassium-t-butoxide in 70 ml of THF was added dropwise over a period of 15 minutes and the mixture was stirred for 1 hr. To this mixture was added dropwise a solution of 18.53 g (74 mmol) of 4-(trans-4-pentylcyclohexyl)cyclohexanone in 74 ml of THF over a period of 25 minutes. The mixture was stirred as such overnight and raised to room temperature. Water and toluene were added, the precipitate was filtered through Celite, and an organic layer and an aqueous layer were separated. The aqueous layer was extracted with toluene, an extract combined with the organic layer was washed with water, and dried over anhydrous magnesium sulfate. Triphenylphosphine oxide in the extract was filtered off, the solvent was distilled off and the solution was condensed. The concentrate was purified by column chromatography (elution solvent: heptane:ethyl acetate=20:1) to obtain 19.67 g of the eluate. Recrystallization at −30° C. from 50 ml of heptane-trace amount of solmix gave 14.31 g of the title compound (52%, Cr 38.4-38.5 Iso).

1. customdried
2. addition74 ml of THF were added
3. stirringThe mixture was stirred as such overnight
4. temperatureraised to room temperature
5. filtrationthe precipitate was filtered through Celite
6. customan organic layer and an aqueous layer were separated
7. extractionThe aqueous layer was extracted with toluene
8. washwas washed with water
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationTriphenylphosphine oxide in the extract was filtered off
11. distillationthe solvent was distilled off
12. customcondensed
13. customThe concentrate was purified by column chromatography (elution solvent: heptane:ethyl acetate=20:1)
14. customto obtain 19.67 g of the eluate
15. customRecrystallization at −30° C. from 50 ml of heptane-trace amount of solmix