Reaktion #6690

Reaktionsgleichung

4-bromobutan-1-ol

3,4-dihydropyran

potassium carbonate

→

2-(4-bromobutoxy)-tetrahydropyran

2-(4-Bromobutoxy)-tetrahydropyran

Lösungsmittel

dichloromethane

phosphorus oxychloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1 h
2. 2
   Sonstigequenched with water
3. 3
   Extraktionextracted with dichloromethane
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigePurification by chromatography on silica gel (5% EtOAc/hexanes)

Vorschrift

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%).

Quelle