反应详情

温度

40 °C

To a solution of 2 (10 g, 32.21 mmol), 4′-hydroxy-biphenyl-4-carbonitrile (6.35 g, 32.53 mmol), and toluenesulfonic/4-(dimethylamino)pyridine complex (0.95 g, 3.22 mmol) in anhydrous methylene chloride (100 mL) was added N,N-dicyclohexylcarbodiimide (6.98 g, 33.82 mmol) under argon. The reaction mixture was stirred at 40° C. overnight. Upon filtering off the white residues, the filtrate was diluted with additional methylene chloride. The solution was then washed with water. The silyl ether of the title compound was purified by flash column chromatography on silica gel with gradient elution from 0 to 2% acetone in methylene chloride. The silyl-protected compound was hydrolyzed in tetrahydrofuran: water:acetic acid (80 mL: 80 mL: 240 mL) overnight. The volume of the solution was reduced by 50% via evaporation under reduced pressure. Methylene chloride was added to the slurry for washing sequentially with H2O, a 10% NaHCO3 solution and brine before drying over anhydrous MgSO4. The crude product resulting from evaporation of the solvent was purified by recrystallization from ethanol to yield 3 (10.71 g, 89%). 1H NMR spectral data (400 MHz, CDCl3): δ 2.10 (quintet, 2H, —CH2—), δ 3.95 (t, 2H, —CH2OAr), δ 4.25 (t, 2H, HOCH2—), δ 7.00–8.25 (m, 12H, aromatic rings).

1. filtrationUpon filtering off the white residues
2. additionthe filtrate was diluted with additional methylene chloride
3. washThe solution was then washed with water
4. customThe silyl ether of the title compound was purified by flash column chromatography on silica gel with gradient elution from 0 to 2% acetone in methylene chloride
5. customacetic acid (80 mL: 80 mL: 240 mL) overnight
6. customThe volume of the solution was reduced by 50% via evaporation under reduced pressure
7. additionMethylene chloride was added to the slurry
8. washfor washing sequentially with H2O
9. dry with materiala 10% NaHCO3 solution and brine before drying over anhydrous MgSO4
10. customThe crude product resulting from evaporation of the solvent
11. customwas purified by recrystallization from ethanol