Réaction #6684

Équation de réaction

4-bromobutan-1-ol

3,4-dihydropyran

potassium carbonate

→

2-(4-bromobutoxy) -tetrahydropyran

2-(4-Bromobutoxy)tetrahydropyran

Solvants

dichloromethane

phosphorus oxychloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1 h
2. 2
   Autrequenched with water
3. 3
   Extractionextracted with dichloromethane
4. 4
   Lavagewashed with brine
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutrePurification by chromatography on silica gel (5% EtOAc (ethylacetate)/hexanes)

Mode opératoire

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 (ethylacetate)/hexanes) afforded 2-(4-bromobutoxy) -tetrahydropyran (18), as a colorless oil (88%).

Source