反応 #450162

反応方程式

diethyl ether

ammonium chloride

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

N,N-dimethylformamide

→

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

溶媒

tetra-hydrofuran

反応条件

後処理

1. 1
   その他at -65° C.
2. 2
   その他in 10 minutes
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with water
5. 5
   乾燥a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
6. 6
   その他The solvent was removed by distillation under reduced pressure
7. 7
   その他The residue thus obtained
8. 8
   その他was purified by column chromatography (eluant: toluene/ethyl acetate=15/1)

実験手順

8.1 g of 5-bromo-1-(tetrahydropyran-2-yloxy)indane was dissolved in 100 ml of anhydrous tetra-hydrofuran under a nitrogen atmosphere. To the solution was dropwise added 20 ml of a 1.5N n-butyllithium-hexane solution at -65° C. in 10 minutes. The resulting mixture was stirred at the same temperature for 5 minutes. Thereto was added 2.3 ml of anhydrous N,N-dimethylformamide. The reaction mixture was heated to room temperature and added to a mixture of 100 ml of ice water, 100 ml of diethyl ether and 2 g of ammonium chloride. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, 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 6.5 g of 5-formyl-1-(tetrahydropyran-2-yloxy)indane.

出典