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29th August 2013 @ 15:07

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Reaction information

*#Reaction file  
Scheme_314.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-benzyl-N-(3-heptynyl)amine (309, 0.516 g,  2.01 mmol) in THF (5.0 mL) under argon at –78 °C, nBuLi (0.96 mL, 2.5 M solution in hexanes, 2.41 mmol) was added dropwise.  After 10 minutes, pre-dried dimethyldisulphide (0.26 mL, 2.82 mmol) was added and the reaction warmed to room temperature.  After 12 hours the reaction was quenched with a saturated solution of NaHCO3 (50.0 mL) and the product extracted into diethyl ether (3 x 50 mL).  The combined organic layer was 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, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a pungent yellow oil (0.463 g, 1.53 mmol, 76 %).

*Yield (%)  76
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp109.pdf
DM Thesis_2000_pp40-49.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_314.cdx
DM Thesis_2000_pp109.pdf
DM Thesis_2000_pp40-49.pdf