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30th August 2013 @ 13:59

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Reaction information

*#Reaction file  
Scheme_413.cdx
*Reaction file type CDX
*Procedure  

N-Methyl-allyl-amine (2.28 g, 30.0 mmol) was added dropwise to a stirred solution of 3-bromo-3-butenyl 4-methyl-1-benzenesulphonate (415, 5.58 g, 17.3 mmol) in MeCN (20.0 mL) and K2CO3 (2.3 g, 18.0 mmol).  The solution was heated at 70 °C for 14 hours.  The product of the reaction was 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, 0-50 % Et2O:petroleum including 5 % Et3N) afforded the title product as a pale yellow oil (2.74 g, 13.50 mmol, 78 %).

*Yield (%)  78
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp152.pdf
DM Thesis_2000_pp64.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
DM Thesis_2000_pp64.pdf
Scheme_413.cdx
DM Thesis_2000_pp152.pdf