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2nd September 2013 @ 13:39

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Reaction information

*#Reaction file  
Scheme_592.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of triethylamine (1.0 mL, 10.0 mmol) and methanesulphonyl chloride (354 mg, 3.5 mmol) in DCM (10.0 mL), 3-(3-methoxy-phenyl)-prop-2-yn-1-ol (486 mg, 3.0 mmol) was added under argon at 0 °C.  The solution was stirred for 20 minutes at -20 °C, before quenching with a solution of ether (30.0 mL), cold filtered, and the solvent removed under reduced pressure.  The product was dissolved in EtOH (10.0 mL), and methylamine (66 % solution in IMS, 3.0 mL, 10.0 mmol) was added at 0 °C.   The resulting solution was refluxed for 30 minutes, before quenching with a saturated solution of NaHCO3 (15.0 mL).  The product was 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 desired compound as a yellow oil (361 mg, 2.1 mmol, 59 %).    

*Yield (%)  59
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp91-95.pdf
DM Thesis_2000_pp185.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_pp91-95.pdf
Scheme_592.cdx
DM Thesis_2000_pp185.pdf