Pyridine → 131719-68-1

To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. After 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%).

1. additionthe reaction mixture was carefully poured onto ice water (100 ml)
2. extractionextracted with diethyl ether (100 ml)
3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customto give the crude product
7. customThis was purified by silica (20 g) column chromatography
8. washeluting with hexane:ethyl acetate (4:1)

ORD record

ord-255bd658ea7d40718910edd4ad580b56

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049444B2