تفاعل #2186185

معادلة التفاعل

compound ( b67 )

3-chloro-2-fluoro-4′-propylbiphenyl-4-ol

potassium carbonate

water

toluene

→

3-chloro-2-fluoro-4-(trans-4-pentyl-cyclohexylmethoxy)-4′-propylbiphenyl

المردود 89.5%

المذيبات

N,N,-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwere added to the reaction mixture
3. 3
   workup.ADDITIONby mixing
4. 4
   workup.WAITThereafter, the mixture was left at rest
5. 5
   أخرىto separate into an organic layer
6. 6
   استخلاصby extracting to the organic layer
7. 7
   غسيلThe resulting organic layer was washed sequentially with water
8. 8
   تركيزa 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure
9. 9
   أخرىto obtain a residue
10. 10
    أخرى7.7 g of the residue was purified by a preparative column chromatography
11. 11
    أخرىfurther purified
12. 12
    أخرىrecrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume)

الإجراء التجريبي

4.0 g of the compound (b67) obtained in the second step was dissolved in 20 mL of N,N,-dimethylformamide. After suspending 2.5 g of potassium carbonate in the solution, 5.6 g of the compound (b68) was added thereto, followed by stirring for 6 hours at 70° C. After completing the reaction, water and toluene were added to the reaction mixture, followed by mixing. Thereafter, the mixture was left at rest to separate into an organic layer and an aqueous layer, followed by extracting to the organic layer. The resulting organic layer was washed sequentially with water, a 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure to obtain a residue. 7.7 g of the residue was purified by a preparative column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=3/1 by volume) as a developing solvent and silica gel as a mediator, and further purified by repeating recrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume) to obtain 3-chloro-2-fluoro-4-(trans-4-pentyl-cyclohexylmethoxy)-4′-propylbiphenyl (C264) as colorless crystals. The yield was 89.5% based on the compound (b67).

المصدر