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16th September 2013 @ 13:37

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a stirred solution of ((3-(1-((3aR,6aR)-5-hexyl-4-phenyl-1,2,3,3a,6,6a-hexahydropentalen-3a-yl)vinyl)benzyl)oxy)triisopropylsilane (1.75 g, 3.14 mmol, 1 equiv.) in THF (40 mL) was added slowly dropwise TBAF (1 M solution in THF, 3.77 mL, 3.77 mmol, 2 equiv.).  The reaction was stirred for 16 hours.

The reaction was diluted with diethyl ether (30 mL) and washed with water (30 mL).  The water layer was washed with diethyl ether (2 x 30 mL).  The diethyl ether layers were combined and washed with water (2 x 50 mL) and brine (50 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure. 

The product was purified by column chromatography (silica gel, 25 % diethyl ether in cyclohexane) to yield the pure product as a yellow oil (0.92 g, 2.29 mmol, 73 % over two steps).  

*Yield (%) 73
*Type of Yield Isolated Product Yield 

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

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 80
For step in multistep reaction - link to following reaction step Reaction 69
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