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2nd September 2013 @ 13:23

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Reaction information

*#Reaction file  
Scheme_562.cdx
*Reaction file type CDX
*Procedure  

To a stirring solution of triethylamine (1 mL, 10.0 mmol) and methanesulphonyl chloride (354 mg, 3.5 mmol) in DCM (10.0 mL), 2-butyn-1-ol (3.0 mmol, 211 mg) was added under argon at 0 °C.  The solution was stirred for 20 minutes at 0 °C, warmed to room temperature and stirred for 20 minutes before quenching with a solution of Et2O (30.0 mL).  The mixture was filtered, and the solvent removed under reduced pressure.  The product was dissolved in MeCN (10.0 mL), N-methyl-N-[(E)-3-phenyl-2-propenyl]amine (556, 2.0 mmol, 294 mg) added at 0 °C, stirred with K2CO3 (1.0 g, 7.5 mmol), triethylamine (3.0 mL) and the solution 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 (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 yellow oil (218 mg, 1.1 mmol, 54 %).    

*Yield (%)  54
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp173.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_562.cdx
DM Thesis_2000_pp173.pdf
DM Thesis_2000_pp81-89.pdf