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16th September 2013 @ 11:09

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Reaction information

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

To a stirred solution of 4-pentyn-1-ol (1.57 mL, 16.99 mmol, 1 equiv.) and imidazole (1.74 g, 25.50 mmol, 1.5 equiv.) in DMF (100 mL) was added slowly dropwise triisopropylsilyl chloride (4.00 mL, 18.69 mmol, 1.1 equiv.).  The reaction was stirred at room temperature for 16 hours.

The reaction was poured onto water (100 mL) and the product was extracted into hexane (3 x 100 mL).  The hexane washes were combined and washed with water (2 x 100 mL) and brine (100 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 pure product (3.24 g, 13.45 mmol, 79 %).

*Yield (%) 79
*Type of Yield Isolated Product Yield 
Reference(s) Dussault, P. H.; Eary, C. T.; Woller, K. R. J Org Chem 1999, 12, 340. 
Further information Using the method of Dussault et al

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 59
Attached Files
ReactionScheme.cdx
L.Sayerpp14-15.pdf