反応 #1063720

反応方程式

pyridinium p-toluenesulfonate

5-bromo-1-hydroxyindane

3,4-dihydro-2H-pyran

→

5-bromo-1-(tetrahydropyran-2-yloxy)indane

溶媒

methylene chloride

反応条件

後処理

1. 1
   workup.ADDITIONTo the solution were added, at room temperature
2. 2
   その他The organic layer was separated
3. 3
   洗浄washed with a saturated aqueous sodium chloride solution
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   その他The solvent was removed by distillation under reduced pressure
6. 6
   その他The residue thus obtained
7. 7
   その他was purified by column chromatography (eluant: toluene/ethyl acetate=15/1)

実験手順

9.6 g of 5-bromo-1-hydroxyindane was dissolved in 100 ml of dry methylene chloride. To the solution were added, at room temperature, 570 mg of pyridinium p-toluenesulfonate and 4.5 ml of 3,4-dihydro-2H-pyran. The resulting mixture was stirred at the same temperature for 3 hours. The reaction mixture was added to ice water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=15/1) to obtain 13.1 g of oily 5-bromo-1-(tetrahydropyran-2-yloxy)indane.

出典