All Notebooks | Help | Support | About
29th August 2013 @ 15:28

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file  
Scheme_374.cdx
*Reaction file type CDX
*Procedure  

A solution of 1-bromooct-4-yne (373, 10.0 g, 53.5 mmol) in benzylamine (86.7 mL, 0.79 mol) was refluxed for 16 hours then quenched 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.  The crude reaction mixture was purified by reduced pressure distillation (121 °C and 19 torr) to afford the title compound as a colourless oil [7.56 g, 34.8 mmol, 65 %].

*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp126.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_374.cdx
DM Thesis_2000_pp126.pdf
DM Thesis_2000_pp51-59.pdf