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2nd September 2013 @ 09:38

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Reaction information

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

Methanesulphonylchloride (1.89 g, 16.5 mmol) was added slowly to a solution of 3-phenyl-4-penten-1-ol (2.43 g, 15 mmol) and triethylamine (1.82 g, 18 mmol) in dry DCM (30 mL) at –40 °C, under Ar. After 2 h, the reaction mixture was filtered and the filtrate washed with brine, dried over MgSO4, filtered and concentrated. A solution of the crude mesylate in dry acetone (10 mL) was added to a refluxing solution of sodium iodide (7.5 g, 50 mmol) in dry acetone (50 mL). After 1.5 h, TLC analysis showed complete consumption of starting material and the reaction mixture was allowed to cool. After pouring into saturated Na2S2O3 solution (30 mL), and pentane (30 mL), the aqueous phase was extracted with pentane, and the combined organic phases washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, 10% ether in petrol) to give the desired iodide as a clear, colourless oil (2.509 g, 61%). 

*Yield (%) 61 
*Type of Yield Isolated Product Yield 
Reference(s)
DavidOwenThesis2000pp48,113.pdf
320LABBOOK.JPG
 
Further information Compound 320: 1-Iodo-3-phenyl-4-pentene 

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 319 
For step in multistep reaction - link to following reaction step Reaction 321
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp48,113.pdf
320LABBOOK.JPG