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30th August 2013 @ 14:21

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Reaction information

*#Reaction file  
Scheme_431.cdx
*Reaction file type CDX
*Procedure  3-Bromo-but-3-enyl)-but-2-ynyl-methyl-amine (1.0 mmol, 203 mg) was added to a 25 mL flask, fitted with a reflux condenser, septum and flushed with argon.  Dry THF (10.0 mL) was added, followed by naphthaleneboronic acid (344.0 mg, 2.0 mmol) and PdCl2(PPH3) (0.1 mol eq., 70.0 mg).  To this yellow solution was added a saturated solution of Na2CO3 (50.0 mL) and the heterogeneous solution heated at 70 °C for 12 hours.  When the reaction was complete (absence of vinyl bromide by tlc) the product was extracted into Et2O (3 x 50.0 mL).  The combined organic layer washed with water (3 x 40 mL), brine (50.0 mL) and 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 an orange oil (133 mg, 0.51 mmol, 51 %).   
*Yield (%)  51
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp159.pdf
DM Thesis_2000_pp70-75.pdf
Further information  

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Overall reaction? True
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Attached Files
Scheme_431.cdx
DM Thesis_2000_pp70-75.pdf
DM Thesis_2000_pp159.pdf