반응 #6690

반응 방정식

4-bromobutan-1-ol

3,4-dihydropyran

potassium carbonate

→

2-(4-bromobutoxy)-tetrahydropyran

2-(4-Bromobutoxy)-tetrahydropyran

용매

dichloromethane

phosphorus oxychloride

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1 h
2. 2
   기타quenched with water
3. 3
   추출extracted with dichloromethane
4. 4
   세척washed with brine
5. 5
   건조dried over MgSO4
6. 6
   농축concentrated in vacuo
7. 7
   기타Purification by chromatography on silica gel (5% EtOAc/hexanes)

실험 절차

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%).

출처