All Notebooks | Help | Support | About
29th August 2013 @ 14:53

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file  
*Reaction file type CDX

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
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp100.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp100.pdf