Water → 1-(4-Ethoxy-2,3-difluorophenyl)-4-methoxymethylenecyclohexane

Temperature

-30 °C

Methoxymethyltriphenylphosphonium chloride (dried; 26.3 g) and THF (100 ml) were mixed under a nitrogen atmosphere and cooled to −30° C. Then, potassium t-butoxide (t-BuOK) (8.6 g) was added in twice in the temperature range of −30° C. to −20° C. The stirring was continued at −20° C. for 30 minutes, and the compound (16) (15.0 g) dissolved in THF (100 ml) was added dropwise in the temperature range of −30° C. to −20° C. The reaction mixture was stirred at −10° C. for 30 minutes, poured into a mixture of water (200 ml) and toluene (200 ml), and mixed. The mixture was allowed to separate into organic and aqueous phases, and the extraction into an organic phase was carried out. The organic phase obtained was washed with water, and dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure and the residue was purified by means of column chromatography (silica gel; toluene). The eluent obtained was concentrated under reduced pressure, giving 21.8 g of 1-(4-ethoxy-2,3-difluorophenyl)-4-methoxymethylenecyclohexane (17). The compound obtained (17) was colorless oil.

1. additionwas added dropwise in the temperature range of −30° C. to −20° C
2. additionmixed
3. customto separate into organic and aqueous phases
4. extractionthe extraction into an organic phase
5. customThe organic phase obtained
6. washwas washed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solution obtained
9. concentrationwas concentrated under reduced pressure
10. customthe residue was purified by means of column chromatography (silica gel; toluene)
11. customThe eluent obtained
12. concentrationwas concentrated under reduced pressure

ORD record

ord-6df095c4a62b477b8b170c25ead1dfcf

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08216489B2