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16th September 2013 @ 11:35

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Reaction information

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

To a stirred solution of (3-((trimethylsilyl)ethynyl)phenyl)methanol (4.38 g, 21.43 mmol, 1 equiv.) in THF (40 mL) was added slowly dropwise TBAF (1 M solution in THF, 23.57 mL, 1.1 equiv.).  The reaction was stirred for 16 hours.

The reaction was diluted with diethyl ether (60 mL) and washed with water (100 mL).  The water layer was washed with diethyl ether (2 x 100 mL).  The diethyl ether layers were combined and washed with water (2 x 100 mL) and brine (100 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure. 

The product was purified by column chromatography (silica gel, 33 % ethyl acetate in hexane) to yield the pure product as a yellow oil (2.78 g, 21.04 mmol, 98 %). 

*Yield (%) 98
*Type of Yield Isolated Product Yield 
Reference(s)

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

L.Sayerpp20.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 51 
For step in multistep reaction - link to following reaction step Reaction 60
Attached Files
L.Sayerpp20.pdf
ReactionScheme.cdx