反応 #6690

反応方程式

4-bromobutan-1-ol

3,4-dihydropyran

potassium carbonate

→

2-(4-bromobutoxy)-tetrahydropyran

2-(4-Bromobutoxy)-tetrahydropyran

溶媒

dichloromethane

phosphorus oxychloride

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1 h
2. 2
   その他quenched with water
3. 3
   抽出extracted with dichloromethane
4. 4
   洗浄washed with brine
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他Purification by chromatography on silica gel (5% EtOAc/hexanes)

実験手順

To a solution of commercially available 4-bromobutan-1-ol (16) (1 equi.) and 3,4-dihydropyran (17) (1.5 equi.) in dichloromethane (3 mL/mmole), phosphorus oxychloride (0.01 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h. Then potassium carbonate (1 equi.) was added to the reaction mixture and the reaction mixture was stirred at room temperature for 1 h, quenched with water, extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) afforded 2-(4-bromobutoxy)-tetrahydropyran (18), as a colorless oil (88%).

出典