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2nd September 2013 @ 13:24

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Reaction information

*#Reaction file  
Scheme_563.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-methyl-N-[(E)-3-phenyl-2-propenyl]amine (556, 298 mg, 2.0 mmol), (3-bromo-prop-1-ynyl)-trimethyl-silane (403 mg, 2.1 mmol) was added dropwise at 0 °C, then heated at 34 °C for 5 minutes. The solution quenched with a saturated solution of NaHCO3 (30.0 mL), filtered, and the solvent removed under reduced pressure.  The product dissolved in MeCN (10.0 mL), (3-bromo-prop-1-ynyl)-trimethyl-silane (2.0 mmol, 296 mg) added at 0 °C, stirred with K2CO3 (1.0 g, 7.5 mmol), triethylamine (3.0 mL) and refluxed for 30 minutes.  The reaction was quenched with a solution of NaHCO3 (15.0 mL), the product extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 30.0 mL), brine (30.0 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 clear oil (335 mg, 1.3 mmol, 68 %).

 

*Yield (%)  68
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp174.pdf
DM Thesis_2000_pp81-89.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
Scheme_563.cdx
DM Thesis_2000_pp174.pdf
DM Thesis_2000_pp81-89.pdf