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16th September 2013 @ 11:31

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Reaction information

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

To a stirred mixture of 3-bromobenzalcohol (1.87 g, 9.55 mmol, 1 equiv.), bis-triphenylphosphine palladium dichloride (0.07 g, 0.1 mmol, 0.01 equiv.), copper iodide (0.02 g, 0.1 mmol, 0.01 equiv.) and triethylamine (25 mL) was added dropwise trimethylsilyl acetylene (1.50 mL, 10 mmol, 1.1 equiv.).  The reaction was heated to 70 °C and stirred for 2 days.

The reaction was diluted with diethyl ether (75 mL) and filtered through celite before being washed with water (4 x 100 mL) and brine (100 mL).  The diethyl ether layer was dried over magnesium sulphate, filtered and concentrated under reduced pressure.

The product was purified by column chromatography (silica gel, 25 % diethyl ether in hexane) to yield the pure product (1.60 g, 7.84 mmol, 82 %). 

*Yield (%) 82
*Type of Yield Isolated Product Yield 
Reference(s)

Takacs, J. M.; Zhang, Q. Org Lett 2008, 10, 545.

L.Sayerpp19-20.pdf
Further information Using the method of Takacs et al

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step Reaction 50 
For step in multistep reaction - link to following reaction step Reaction 52
Attached Files
L.Sayerpp19-20.pdf
ReactionScheme.cdx