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29th August 2013 @ 14:58

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Reaction information

*#Reaction file  
Scheme_310.cdx
*Reaction file type CDX
*Procedure  

4-Bromo-1-butene (0.608 g, 4.5 mmol) was added dropwise to a stirring solution of N-benzyl-N-(3-heptynyl)amine (309, 1.0 g, 4.3 mmol) in MeCN (10.0 mL) and K2CO3 (1.0 g, 12 mmol) at 0 °C.  The solution was refluxed for 4 hours then quenched with saturated NaHCO3 solution (50.0 mL).  The product was extracted into diethyl ether (3 x 50 mL) washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Chromatography (SiO2, 0-50 % Et2O:petroleum including 5 % Et3N) afforded the title product as a viscous orange oil (0.99 g,  3.7 mmol,  85 %).

*Yield (%)  85
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp104.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_310.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp104.pdf