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2nd September 2013 @ 13:12

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Reaction information

*#Reaction file  
Scheme_533.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-methyl-N-(2-phenylallyl)amine (530, 296 mg, 2.0 mmol), K2CO3 (1.0 g, 7.5 mmol), MeCN (10.0 mL), propargyl bromide (354 mg, 3.0 mmol) was added dropwise.  The solution was refluxed for 12 hrs then quenched with a saturated solution of NaHCO3 (30 mL).  The product 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, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as an orange oil (251 mg,  1.4 mmol, 68 %). 

*Yield (%)  68
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp164.pdf
DM Thesis_2000_pp81-89.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_533.cdx
DM Thesis_2000_pp164.pdf
DM Thesis_2000_pp81-89.pdf