反应 #6690

反应方程式

4-bromobutan-1-ol

3,4-dihydropyran

potassium carbonate

→

2-(4-bromobutoxy)-tetrahydropyran

2-(4-Bromobutoxy)-tetrahydropyran

溶剂

dichloromethane

phosphorus oxychloride

反应条件

后处理

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

实验过程

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%).

来源