Water → 1-(3-Fluorophenyl)-4-methoxymethylenecyclohexane

Temperatur

-30 °C

Well-dried methoxymethyltriphenylphosphonium chloride (112.1 g) and THF (1000 ml) were mixed under a nitrogen atmosphere, and cooled to −30° C. Then, potassium t-butoxide (t-BuOK; 36.7 g) was put in thereto in twice in the temperature range of −30° C. to 20° C. After the mixture had been stirred at −20° C. for 30 minutes, the compound (35) (41.9 g) dissolved in THF (200 ml) was added dropwise thereto in the temperature range of −30° C. to −20° C. After the reaction had been stirred at −10° C. for 30 minutes, it was poured into a mixture of water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The eluent obtained was concentrated under reduced pressure, giving 45.0 g of 1-(3-fluorophenyl)-4-methoxymethylenecyclohexane (36). The yield based on the compound (35) was 93.7%.

1. customtwice in the temperature range of −30° C. to 20° C
2. additionwas added dropwise
3. customin the temperature range of −30° C. to −20° C
4. stirringAfter the reaction had been stirred at −10° C. for 30 minutes
5. additionmixed
6. customhad separated into two phases of organic and aqueous phases
7. customThe organic phase obtained
8. washwashed with water
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solution obtained
11. concentrationwas concentrated under reduced pressure
12. customthe residue obtained
13. customwas purified with a fractional operation by means of column chromatography
14. customThe eluent obtained
15. concentrationwas concentrated under reduced pressure

ORD-Eintrag

ord-a687abd53ce2486e8692a66ac0b3a43d

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08187494B2