反応 #1973904

反応方程式

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

収率 98.3%

溶媒

THF

toluene

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise in the temperature range of −30 to −20° C
2. 2
   workup.ADDITIONmixed with it
3. 3
   その他had separated into two phases of organic and aqueous phases
4. 4
   抽出the extraction into an organic phase
5. 5
   その他The resulting organic phase was separated
6. 6
   洗浄washed with water
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   濃縮The resulting solution was concentrated under reduced pressure
9. 9
   その他the resulting residue was purified with a fractional operation by means of column chromatography
10. 10
    濃縮The resulting eluent was concentrated under reduced pressure

実験手順

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%.

出典