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2nd September 2013 @ 13:13

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Reaction information

*#Reaction file  
Scheme_535.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-methyl-N-(2-phenylallyl)amine (530, 512 mg, 2.0 mmol), (3-bromo-prop-1-ynyl)-trimethyl-silane (382 mg, 2.0 mmol) was added dropwise, heated at 80 °C for 12 hours, before quenching 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, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a viscous oil (363 mg, 1.4 mmol, 71 %).

*Yield (%)  71
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp165.pdf
DM Thesis_2000_pp81-89.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_535.cdx
DM Thesis_2000_pp165.pdf
DM Thesis_2000_pp81-89.pdf