Water → 1-Ethoxy-2,3-difluoro-4-[4-(2-methoxyvinyl)-cyclohexyl]benzene

In a reactor under nitrogen atmosphere, 25 mL of THF was added to 7.7 g of methoxymethyltriphenylphosphonium chloride, and the mixture was cooled to −20° C., to which 2.5 g of t-BuOK was added, followed by stirring for 1 hour A solution containing 5.0 g of 4-(4-ethoxy-2,3-difluorophenyl)cyclohexane-carboaldehyde dissolved in 50 mL of THF was added dropwise thereto, followed by stirring for 1 hour. The temperature of the reaction mixture was increased to room temperature, and 100 mL of water was added to the reaction mixture, followed by extracting three times with 100 mL of toluene. The resulting organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was concentrated to about 100 mL under reduced pressure, and the concentrated solution was placed in 500 mL of toluene, followed by removing deposited solid matters. The solvent was distilled off from the resulting solution under reduced pressure, and the residue was purified by silica gel column chromatography to provide 4.9 g of 1-ethoxy-2,3-difluoro-4-[4-(2-methoxyvinyl)-cyclohexyl]benzene.

1. additionwas added
2. additionwas added dropwise
3. stirringby stirring for 1 hour
4. extractionby extracting three times with 100 mL of toluene
5. washThe resulting organic layer was washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationthe solvent was concentrated to about 100 mL under reduced pressure
8. customby removing
9. distillationThe solvent was distilled off from the resulting solution under reduced pressure
10. customthe residue was purified by silica gel column chromatography

ORD record

ord-d667f1e003e74ae894dc7e0e5f41e975

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372306B2