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29th August 2013 @ 15:03

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Reaction information

*#Reaction file  
Scheme_311.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-benzyl-N-(3-pentynyl)amine (308, 173 mg, 1.0 mmol), K2CO3 (1.0 g, 10.0 mmol) and MeCN (10.0 mL), benzenesulfonate (306, 238 mg, 1.0 mmol) was added dropwise, refluxed for 24 hrs, quenched with a saturated solution of NaHCO3 (20.0 mL).  The product was extracted into diethyl ether (3 x 25 mL), the combined organic layer washed with water (3 x 25 mL), brine (25.0 mL), 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 pale oil (100 mg, 0.4 mmol, 40 %).

 

*Yield (%)  40
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp105.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
Scheme_311.cdx
DM Thesis_2000_pp105.pdf
DM Thesis_2000_pp40-49.pdf