反应详情

温度

0 °C

To 600 ml of THF was added 60 g (0.18 mol) of dried methoxymethyltriphenylphosphonium chloride and the mixture was cooled to 0° C. 20 g (0.18 mol) of potassium t-butoxide was gradually added thereto, and the mixture was stirred for 2 hours as at that temperature. To the reaction solution was added dropwise a solution of 26 g (0.12 mol) of 4-(3,5-difluorophenyl)cyclohexanone obtained above in 200 ml of THF, and the mixture was warmed to room temperature and stirred for 10 hours. After adding water to the reaction solution, the reaction product was extracted with toluene, the extract was washed with water and the solvent was distilled off. The residue was purified by column chromatography on silica gel (eluting solvent: toluene) and the solvent was distilled off under reduced pressure. The residue thus obtained was added to a mixed solvent of 300 ml of 3N hydrochloric acid and 600 ml of acetone and the mixture was stirred for 3 hours. The reaction product was extracted with toluene, the extract was washed successively with a saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate, and the solvent was then distilled off. The residue thus obtained, 1 g of p-toluenesulfonic acid and 14 g of trimethylene glycol were refluxed in 200 ml of toluene for 3 hours. The reaction solution was washed successively with a saturated aqueous sodium bicarbonate and water, and the solvent was then distilled off. The residue was purified by column chromatography on silica gel (eluting solvent: toluene) and the solvent was then distilled off under reduced pressure to afford 30 g (0.11 mol) of 4-(3,5-difluorophenyl)cyclohexanecarboaldehyde propylene ketal.

1. temperaturethe mixture was warmed to room temperature
2. stirringstirred for 10 hours
3. extractionthe reaction product was extracted with toluene
4. washthe extract was washed with water
5. distillationthe solvent was distilled off
6. customThe residue was purified by column chromatography on silica gel (eluting solvent: toluene)
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue thus obtained
9. stirringthe mixture was stirred for 3 hours
10. extractionThe reaction product was extracted with toluene
11. washthe extract was washed successively with a saturated aqueous sodium bicarbonate and water
12. dry with materialdried over magnesium sulfate
13. distillationthe solvent was then distilled off
14. customThe residue thus obtained
15. washThe reaction solution was washed successively with a saturated aqueous sodium bicarbonate and water
16. distillationthe solvent was then distilled off
17. customThe residue was purified by column chromatography on silica gel (eluting solvent: toluene)
18. distillationthe solvent was then distilled off under reduced pressure