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2nd September 2013 @ 13:20

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Reaction information

*#Reaction file  
Scheme_559.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-benzylallylamine (1.46g, 10.0 mmol), K2CO3 (2.0 g, 20.0 mmol) in MeCN (30.0 mL) at 0 °C, cinnamyl bromide (1.97 g, 10.0 mmol) was added dropwise.  The solution was warmed to room temperature, stirred for 1 hour then refluxed for 1 hour, quenched with a saturated solution of NaHCO3 (50.0 mL).  The product was extracted into diethyl ether (3 x 40 mL), the combined organic layer washed with water (3 x 30 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 (2.31 g, 8.7 mmol, 87 %). 

*Yield (%)  87
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp81-89.pdf
DM Thesis_2000_pp171.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_559.cdx
DM Thesis_2000_pp171.pdf
DM Thesis_2000_pp81-89.pdf