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30th August 2013 @ 14:05

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Reaction information

*#Reaction file  
Scheme_415.cdx
*Reaction file type CDX
*Procedure  

3-Bromo-3-buten-1-ol (416, 10.0 g, 66.2 mmol) was added to para-tolulenesulphonyl chloride (13.3 g, 70 mmol) in anhydrous pyridine (18.8 g, 238 mmol) at 0-5 °C.  After stirring for 12 hours, the reaction mixture was cooled to 0 °C and HCl (6M, 6.0 mL) was added.  The product was extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (4 x 50 mL), brine (50.0 mL), filtered, dried over MgSO4, filtered and the solvent removed under reduced pressure. Column chromatography (SiO2, 0-50 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a yellow oil (15.18 g, 50.0 mmol, 75  %).

*Yield (%)  75
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp64.pdf
DM Thesis_2000_pp153.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
DM Thesis_2000_pp64.pdf
Scheme_415.cdx
DM Thesis_2000_pp153.pdf