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29th August 2013 @ 15:30

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Reaction information

*#Reaction file  
Scheme_377.cdx
*Reaction file type CDX
*Procedure  

Propargyl bromide (80 % wt. in toluene, 2.67 mL, 30.0 mmol) was added dropwise to a stirred solution of N-benzyl-N-(4-octynyl)amine (374, 6.52 g, 30 mmol), K2CO3 (2.0 g, 20 mmol) and MeCN (20 mL), refluxed for 8 hours, quenched with a saturated solution of NaHCO3 (20.0 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 and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-50 % Et2O:petrol including 5 % Et3N) afforded the title product as a viscous yellow oil (5.1 g, 23 mmol, 76 %). 

*Yield (%)  76
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp128.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_377.cdx
DM Thesis_2000_pp128.pdf
DM Thesis_2000_pp51-59.pdf