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2nd September 2013 @ 13:14

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Reaction information

*#Reaction file  
Scheme_536.cdx
*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
Reference(s)  
DM Thesis_2000_pp166.pdf
DM Thesis_2000_pp81-89.pdf
Further information  

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Overall reaction? True
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Attached Files
Scheme_536.cdx
DM Thesis_2000_pp166.pdf
DM Thesis_2000_pp81-89.pdf