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2nd September 2013 @ 13:13

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Reaction information

*#Reaction file  
*Reaction file type CDX

To a stirred solution of N-methyl-N-(2-phenylallyl)amine (530, 512 mg, 2.0 mmol), (3-bromo-prop-1-ynyl)-trimethyl-silane (382 mg, 2.0 mmol) was added dropwise, heated at 80 °C for 12 hours, before quenching with a saturated solution of NaHCO3 (20.0 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) afforded the title compound as a viscous oil (363 mg, 1.4 mmol, 71 %).

*Yield (%)  71
*Type of Yield Isolated product yield
DM Thesis_2000_pp165.pdf
DM Thesis_2000_pp81-89.pdf
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Overall reaction? True
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Attached Files
DM Thesis_2000_pp165.pdf
DM Thesis_2000_pp81-89.pdf