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30th August 2013 @ 14:52

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Reaction information

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

To a solution of tert-butyldimethyl((4-(3-methyltetrahydro-2H-2-pyranyliden) butyl)oxy)silane (210) (227 mg, 0.8 mmol) in THF (5 mL) was added dropwise tetrabutyl ammonium fluoride (1.2 mL of a 1 M solution in THF, 1.2 mmol) and the solution stirred for 1 h, whereupon H2O (10 mL) and ether (10 mL) were added. The phases were separated, and the aqueous extracted with ether. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. To this crude product was added DCM (10 mL) and camphor sulfonic acid (20 mg, 0.08 mmol). After stirring for 1h, TLC analysis showed absence of the starting alcohol, and water (10 mL) was added to the reaction mixture. The phases were separated and the organic layer dried over Na2SO4, filtered and concentrated to a volume of about 5 mL. This crude solution was subjected to column chromatography (SiO2, 10% ether in pentane) to provide the title compound as a colourless oil (50 mg, 0.29 mmol, 37%). GC analysis showed the product to be a 4:1 mixture of diastereomers (HP-5 column, conditions: 60 °C for 4 min, then increase at 15 °C / min to 250 °C. Retention times: 9.30 min (major), 9.60 min (minor)).  

*Yield (%) 37
*Type of Yield Reaction Yield 
Reference(s)

H. Oikawa, M. Oikawa, A. Ichihara, K. Kobayashi, M. Uramoto, Tetrahedron Lett. 1993, 34, 5303.
M. Oikawa, H. Oikawa, A. Ichihara, Tetrahedron 1995, 51, 6237.

DavidOwenThesis2000pp37,38,97,98.pdf
212LABBOOK.JPG
 
Further information Compound 212: 5-Methyl-1,7-dioxaspiro[5.5]undecane

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 
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp37,38,97,98.pdf
212LABBOOK.JPG