反应详情

16.4 g of the compound (8), 0.2 g of p-toluenesulfonic acid and 80 mL of toluene were mixed, and the mixture was refluxed under heating for 2 hours while water distilled out was removed. After cooling the resulting reaction mixture to 25° C., 200 mL of water and 200 mL of toluene were added to and mixed with the reaction mixture, which was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=4/1 by volume) as eluent, and then further purified by recrystallization from a mixed solvent of heptane and ethanol (heptane/ethanol=2/1 by volume) to obtain 6.2 g of 2-chloro-4-ethoxy-3-fluoro-1-(4-(2-(trans-4-propylcyclohexyl)-2-ethyl)-cyclohexa-1-enyl)benzene (No. 103). The yield based on the compound (7) was 42.4%.

1. temperaturethe mixture was refluxed
2. distillationdistilled out
3. customwas removed
4. temperatureAfter cooling
5. customthe resulting reaction mixture to 25° C.
6. additionmixed with the reaction mixture, which
7. customwas separated into an organic layer
8. extractionextraction to the organic layer
9. washwashed with a 2N sodium hydroxide aqueous solution
10. dry with materialby drying over anhydrous magnesium sulfate
11. distillationThereafter, the solvent was distilled off under reduced pressure
12. customto obtain a residue
13. customThe resulting residue was purified by silica gel column chromatography
14. customfurther purified by recrystallization from a mixed solvent of heptane and ethanol (heptane/ethanol=2/1 by volume)