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16th September 2013 @ 11:20

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a stirred solution of triisopropyl(pent-4-yn-1-yloxy)silane (3.00 g, 12.48 mmol, 1 equiv.) in THF (40 mL) at -78  °C was added slowly dropwise n-butyl lithium (2.5 M in hexanes, 5.99 mL, 14.98 mmol, 1.2 equiv.).  The reaction was warmed to -50 °C and HMPA (3.26 mL, 18.72 mmol, 1.5 equiv.).  The reaction was stirred for 20 minutes at this temperature before being allowed to warm to room temperature and stirred for 16 hours.

The reaction was quenched with ammonium chloride solution (sat. aq., 40 mL) and the product was extracted into diethyl ether (3 x 30 mL).  The diethyl ether washes were combined and washed with water (3 x 50 mL) and brine (50 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure.

The product was purified by column chromatography (silica gel, 2 % diethyl ether in hexane) to yield the product (1.87 g, 6.07 mmol, 49 %). 

*Yield (%) 49
*Type of Yield Isolated Product Yield 
Further information

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 57 
For step in multistep reaction - link to following reaction step Reaction 79
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