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30th August 2013 @ 14:45

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a solution of ZrCp­2Cl2 (375 mg, 1.29 mmol) in THF (5 mL) at –80 °C under Ar was added n-butyllithium (1.03 mL of a 2.5 M solution in hexanes, 2.58 mmol). After 10 minutes, ((6-(4-pentenyloxy)-5-hexynyl)oxy)-(tert-butyl)dimethylsilane (209) (347 mg, 1.17 mmol) in THF (2 mL) was added. The solution was allowed to warm to room temperature and after 4 h MeOH (2 mL) and saturated NaHCO3 solution (4 mL) were added. After stirring over night the mixture was poured into water and ether, and the layers separated. The aqueous phase was extracted with ether, and the combined organic extracts washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (neutral alumina, 10% ether in petrol) to provide the desired compound as a colourless oil (189 mg, 0.63 mmol, 54%). 

*Yield (%) 54 
*Type of Yield Isolated Product Yield 
Further information Compound 211: tert-Butyldimethyl((5-(3-methyltetrahydro-2H-2-pyranyliden)pentyl)oxy) silane

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 209 
For step in multistep reaction - link to following reaction step N/A
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