反应 #1973904

反应方程式

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

收率 98.3%

溶剂

THF

toluene

THF

反应条件

后处理

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

实验过程

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%.

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