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2nd September 2013 @ 13:19
This post is compatible for submission to ChemSpider Reactions. See [blog=44639]ChemSpider Reactions template - help and further information[/blog] for help when using it. Reaction information *#Reaction file  [data]39734[/data] *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)  [data]39736[/data][data]39738[/data] 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