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30th August 2013 @ 14:56

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Reaction information

*#Reaction file
*Reaction file type CDX

To a solution of tert-butyldimethyl((5-(3-methyltetrahydro-2H-2-pyranyliden) pentyl)oxy)silane (169 mg, 0.5 mmol) in THF (3 mL) was added dropwise TBAF (0.75 mL of a 1 M solution in THF, 0.75 mmol). After stirring for 1 h, water (8 mL) was added, the phases separated, and the aqueous extracted with ether. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. DCM (8 mL) was added to the concentrate, followed by camphor sulfonic acid (20 mg). After 1 h, TLC analysis showed complete conversion, and water (10 mL) was added. The organic phase was separated, dried over Na2SO4, filtered and concentrated to a volume of about 3 mL. This solution was subjected to column chromatography (SiO2, 10% ether in pentane) to provide the desired product as a colourless oil (46 mg, 0.25 mmol, 50%). GC analysis showed the product to be an 11:1 mixture of diastereomers (HP-5 column, conditions: 60 °C for 4 min, then increase at 15 °C / min to 250 °C. Retention times: 11.35 min (major), 11.64 min (minor)). 

*Yield (%) 50
*Type of Yield Product Yield 
Further information Compound 213: 5-Methyl-1,7-dioxaspiro[5.6]dodecane

For multistep reactions (or their steps):

Overall reaction? True 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step N/A 
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