反応 #2186185

反応方程式

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

収率 89.5%

溶媒

N,N,-dimethylformamide

反応条件

後処理

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
   その他to separate into an organic layer
6. 6
   抽出by extracting to the organic layer
7. 7
   洗浄The resulting organic layer was washed sequentially with water
8. 8
   濃縮a 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure
9. 9
   その他to obtain a residue
10. 10
    その他7.7 g of the residue was purified by a preparative column chromatography
11. 11
    その他further purified
12. 12
    その他recrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume)

実験手順

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).

出典