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29th August 2013 @ 14:54

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Reaction information

*#Reaction file  
Scheme_307.cdx
*Reaction file type CDX
*Procedure  

3-Heptyn-1-ol (10.0 g, 89.3 mmol) was added to p-toluene sulphonyl chloride (16.9 g, 89.0 mmol) in anhydrous pyridine (39.5 g, 500 mmol) at 0-5 °C.  After stirring overnight at room temperature, the reaction mixture was cooled to 0 °C and 6M HCL (30.0 mL) was added.  The product was extracted into diethyl ether (3 x 100 mL) and the combined organic extracts washed with water (4 x 100 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title product as a yellow oil (17.32 g, 65 mmol, 73 %).

*Yield (%)  73
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp101.pdf
Further information  

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Overall reaction? True
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Attached Files
Scheme_307.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp101.pdf