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29th August 2013 @ 15:06

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Reaction information

*#Reaction file  
*Reaction file type CDX

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
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp108.pdf
Further information  

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Overall reaction? True
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Attached Files
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp108.pdf