All Notebooks | Help | Support | About
2nd September 2013 @ 13:19

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file  
Scheme_558.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-methylallylamine (710 mg, 10.0 mmol), K2CO3 (2.00 g, 20.0 mmol) and MeCN (20 mL), cinnamyl bromide (1.97 g, 10.0 mmol) was added dropwise at 0 °C.  The solution was allowed to warm to room temperature, refluxed for 1 hour, before quenching 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 (1.71 g, 9.1 mmol, 91 %). 

*Yield (%)  91
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp170.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_558.cdx
DM Thesis_2000_pp170.pdf
DM Thesis_2000_pp81-89.pdf