All Notebooks | Help | Support | About
2nd September 2013 @ 13:14

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  
*Reaction file type CDX
*Procedure  To a stirred solution of triethylamine (1.0 mL, 10.0 mmol), methanesulphonyl chloride (354 mg, 3.5 mmol) in DCM (10.0 mL) at 0 °C, 2-butyn-1-ol (3.0 mmol, 211 mg) was added dropwise.  The solution stirred for 20 minutes at 0 °C, warmed to room temperature and stirred for 20 minutes before quenching with Et2O (30.0 mL), filtered and the solvent removed under reduced pressure.  The product was dissolved in MeCN (10.0 mL), then N-Methyl-N-(2-phenylallyl)amine (530, 296 mg, 2.0 mmol) was added to the solution and stirred for 10 minutes.  After this K2CO3 (1.0 g, 9.0 mmol) was added and the solution refluxed for 30 minutes, the reaction was quenched with a saturated solution of NaHCO3 (30.0 mL).  The product was extracted into diethyl ether (2 x 50 mL), the combined organic layer washed with 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 an orange oil (248 mg, 1.2 mmol, 62 %).    
*Yield (%)  62
*Type of Yield Isolated product yield
DM Thesis_2000_pp166.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
DM Thesis_2000_pp166.pdf
DM Thesis_2000_pp81-89.pdf