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29th August 2013 @ 15:26

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Reaction information

*#Reaction file  
Scheme_372.cdx
*Reaction file type CDX
*Procedure  

5-bromopentyne (745 mg, 5.0 mmol) was added dropwise to a stirring solution of N-benzyl-N-allylamine (662 mg, 4.5 mmol), MeCN (10.0 mL) and K2CO3 (3.0 g, 28.0 mmol).  The solution was then refluxed for 10 hours before quenching with a saturated solution of NaHCO3 (10.0 mL). The product was extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4 and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-50 % Et2O:petroleum including 5 % Et3N) afforded the title product as a viscous orange oil (1.02 g,  3.9 mmol,  85 %).

*Yield (%)  85
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp194.pdf
DM Thesis_2000_pp51-59.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_372.cdx
DM Thesis_2000_pp194.pdf
DM Thesis_2000_pp51-59.pdf