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29th August 2013 @ 15:06

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Reaction information

*#Reaction file  
Scheme_313.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-(3-heptynyl)-N-methylamine (0.63 g, 5.0 mmol), K2CO3 (1.2 g, 12.0 mmol) and MeCN (5 mL), benzenesulfonate (307, 1.33 g, 5.0 mmol) was added dropwise.  The solution was refluxed for 15 hrs then quenched with NaOH (6 M, 20.0 mL).  The product extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 100 mL), brine (50.0 mL), dried over MgSO4 and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N), afforded the title compound as a pale oil (0.94 g, 4.3 mmol, 86 %).

*Yield (%)  86
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp108.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_313.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp108.pdf