All Notebooks | Help | Support | About
30th August 2013 @ 14:52

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file
*Reaction file type CDX 

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 

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.

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