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30th August 2013 @ 14:42

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Reaction information

*#Reaction file
*Reaction file type CDX 

n-Butyllithium (4.2 mL of a 2.5 M solution in hexanes, 10.5 mmol) is added dropwise to a solution of (4-iodobutoxy)(tert-butyl)dimethyl silane (905 mg, 5 mmol) in THF (8 mL) at –78 °C (internal thermometer) under Ar. After 30 minutes at below –70 °C, the solution is allowed to warm to –40 °C over 30 minutes. The appropriate iodide (5 mmol) in HMPA (2 mL) is added, and the resultant orange solution stirred to room temperature for 4 h. MeOH (3 mL) is added to the dark red solution, and the mixture poured into cold saturated NH4Cl solution (20 mL) and pentane (20 mL). The aqueous layer is separated, and extracted into pentane (3 x 20 mL). The combined organic phases are washed with water then brine, dried over Na2SO4, filteredand concentrated, to give a brown oil. The crude product is purified by column chromatography (neutral alumina, petrol) to give ((6-(4-Pentenyloxy)-5-hexynyl)oxy)-(tert-butyl)dimethylsilane in 26% yield.  

*Yield (%) 26
*Type of Yield Isolated Product Yield 
Further information Compound 209: ((6-(4-Pentenyloxy)-5-hexynyl)oxy)-(tert-butyl)dimethylsilane

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 N/A 
For step in multistep reaction - link to following reaction step Reaction 211
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