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30th August 2013 @ 13:01

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Reaction information

*#Reaction file  
Scheme_380.cdx
*Reaction file type CDX
*Procedure  

To a stirring solution of 2-bromobenzaldehyde (1.85 g, 1.17 mL, 10.0 mmol), 1-pentyne (750 mg, 1.1 mL), CuI (100 mg, 0.50 mmol), triphenylphosphine (100 mg, 0.40 mmol) and Et3N (20 mL), bis-triphenylphosphinepalladium(II) chloride (100 mg, 0.14 mmol) was added dropwise.  The reaction was refluxed for 17 hours before quenching with a saturated solution of NaHCO3 (20.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combiner 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) afforded the title compound as a red oil (9.00 g, 9.0 mmol, 90 %).

*Yield (%)  90
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp130.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_380.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp130.pdf