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16th September 2013 @ 11:14

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Reaction information

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

To a stirred solution of phenyl acetylene (5.10 mL, 46.42 mmol, 1.1 equiv.) in THF (60 mL) at -78 °C was added slowly dropwise n-butyl lithium (2.5 M in hexanes, 18.57 mL, 46.42 mmol, 1.1 equiv.).  The reaction mixture was warmed to -55 °C and HMPA (11.01 mL, 63.30 mmol, 1.5 equiv.) was added slowly dropwise.  The reaction was stirred at this temperature for 20 minutes before 5-bromopent-1-ene (5.00 mL, 42.20 mmol, 1 equiv.) in THF (20 mL) was added slowly dropwise.  The reaction was stirred for 16 hours.

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

The product was purified by column chromatography (silica gel, hexane) to yield the pure product as a colourless oil (5.81 g, 34.11 mmol, 73 %). 

*Yield (%) 73
*Type of Yield Isolated Product Yield 
Reference(s)

Kobayashi, T.; Koga, Y.; Narasaka, K. J Organomet Chem 2001, 624, 73.

L.Sayerpp15-16.pdf
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 N/A 
For step in multistep reaction - link to following reaction step Reaction 76
Reaction 77
Reaction 80 
Attached Files
ReactionScheme.cdx
L.Sayerpp15-16.pdf