Water → HCID 66876520, compound

In a reactor under nitrogen atmosphere, 30 mL of THF was added to 9.7 g of methoxymethyltriphenylphosphonium chloride, and the mixture was cooled to −20° C., to which 3.1 g of t-BuOK was added, followed by stirring for 1 hour. A solution containing 6.6 g of 4-(4-ethoxy-2,3-difluorophenoxymethyl)cyclohexane carboaldehyde obtained in the seventh step dissolved in 70 mL of THF was added dropwise thereto, followed by stirring for 1 hour. The temperature of the reaction mixture was increased to room temperature, to which 100 mL of water was added, and the mixture was extracted three times with 100 mL toluene. The resulting organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to about 100 mL, and the concentrated solution was placed in 500 mL of n-hexane, 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 6.5 g of 1-ethoxy-2,3-difluoro-4-[4-(2-methoxyvinyl)cyclohexylmethoxy]benzene.

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

ORD record

ord-1ca8779a8e7847a5acc89b3ee91f45b4

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07914862B2