3,4-dihydro-2H-pyran → 2-(4-Bromobutoxy)tetrahydro-2H-pyran

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%).

1. stirringthe reaction mixture was stirred at room temperature for 1 h
2. customquenched with water
3. extractionextracted with dichloromethane
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customPurification by chromatography on silica gel (5% EtOAc (ethylacetate)/hexanes)

ORD-Eintrag

ord-9c10f800168b48649bfb59f8e3d09d94

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07083832B2