Reaktion #1973904

Reaktionsgleichung

compound ( 24 )

4′-(4-butoxy-2,3-difluorophenyl)-bicyclohexyl-4-one

water

methoxymethyltriphenylphosphonium chloride

potassium t-butoxide

→

4-(4-butoxy-2,3-difluorophenyl)-4′-methoxymethylene-bicyclohexyl

Ausbeute 98.3%

Lösungsmittel

THF

toluene

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise in the temperature range of −30 to −20° C
2. 2
   workup.ADDITIONmixed with it
3. 3
   Sonstigehad separated into two phases of organic and aqueous phases
4. 4
   Extraktionthe extraction into an organic phase
5. 5
   SonstigeThe resulting organic phase was separated
6. 6
   Waschenwashed with water
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   EinengenThe resulting solution was concentrated under reduced pressure
9. 9
   Sonstigethe resulting residue was purified with a fractional operation by means of column chromatography
10. 10
    EinengenThe resulting eluent was concentrated under reduced pressure

Vorschrift

Well-dried methoxymethyltriphenylphosphonium chloride (7.9 g) and THF (100 ml) were mixed under an atmosphere of nitrogen, and cooled to −30° C. Then, potassium t-butoxide (t-BuOK) (2.6 g) was added in four portions in the temperature range of −30° C. to −20° C. After the stirring at −20° C. for another 30 minutes, the compound (24) (6.8 g) dissolved in THF (35 ml) was added dropwise in the temperature range of −30 to −20° C. After the mixture had been stirred at −10° C. for 30 minutes, the reaction solution was poured into a mixture water (200 ml) and toluene (100 ml) and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed with water and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure and the resulting residue was purified with a fractional operation by means of column chromatography using silica gel as a stationary phase powder and toluene as an eluent. The resulting eluent was concentrated under reduced pressure to leave 4-(4-butoxy-2,3-difluorophenyl)-4′-methoxymethylene-bicyclohexyl (25) (7.2 g). The yield based on the compound (24) was 95.5%.

Quelle