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30th August 2013 @ 13:00

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Reaction information

*#Reaction file  
Scheme_378.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-benzyl-N-(2-propynyl)-N-(4-octynyl)amine (377, 0.516 g,  2.0 mmol) in THF (5.0 mL) under argon at –78 °C, nBuLi (0.96 mL of 2.5 M solution in hexanes, 2.41 mmol) was added dropwise.  Pre-dried dimethyldisulphide (0.26 mL, 2.82 mmol) was added and the solution warmed to room temperature, stirred for 2 hours before quenching with a saturated solution of NaHCO3 (50.0 mL).  The product 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, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a pungent yellow oil (540 mg, 1.80 mmol, 90 %).

*Yield (%)  90
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp129.pdf
DM Thesis_2000_pp51-59.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_378.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp129.pdf