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29th August 2013 @ 14:53

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Reaction information

*#Reaction file  
Scheme_306.cdx
*Reaction file type CDX
*Procedure  

3-Pentyn-1-ol (2.0 g, 23.81 mmol) was added to p-toluene sulphonyl chloride (4.60 g, 23.81 mmol) in anhydrous pyridine (18.8 g, 238 mmol), at 0-5 °C.  After stirring overnight at room temperature, HCL (6M, 6.0 mL) was added at 0 °C.  The product extracted into diethyl ether (3 x 100 mL), the combined organic extracts washed with water (4 x 50 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 (4.5 g, 19 mmol, 83 %).   

*Yield (%)  83
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp100.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
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Attached Files
Scheme_306.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp100.pdf