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30th August 2013 @ 13:10

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Reaction information

*#Reaction file  
Scheme_389.cdx
*Reaction file type CDX
*Procedure

5-Bromopentene (745 mg, 5.0 mmol) was added dropwise to a stirring solution of methyl-(3-phenyl-prop-2-ynyl)-amine (667 mg, 4.6 mmol), K2CO3 (2.0 g, 20.0 mmol) and MeCN (20.0 mL).  The solution was refluxed for 12 hours before quenching with a saturated solution of NaHCO3 (40.0 mL).  The product was extracted with diethyl ether (3 x 50 mL), the combined organic layer 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 compound as an orange oil (715 mg, 3.4 mmol, 73 %).

 
*Yield (%)  73
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp136.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_389.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp136.pdf