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2nd September 2013 @ 13:10

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Reaction information

*#Reaction file  
Scheme_530.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of methylamine (66 % solution in IMS, 30.0 mL, 787 mmol), 1-[1-(bromomethyl)vinyl]benzene (5.00 g, 26.0 mmol) was added dropwise, and heated at 44 °C for 18 hours before quenching with a saturated solution of NaHCO3 (30.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) and Kugelrohr distillation (7.0 mm Hg, 135 °C) afforded the title compound (451 mg, 3.1 mmol, 61 %). 

*Yield (%)  61
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp162.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_530.cdx
DM Thesis_2000_pp162.pdf
DM Thesis_2000_pp81-89.pdf