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22nd August 2013 @ 09:42

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Reaction information

*#Reaction file  
CSRxnsScheme_94.cdx
*Reaction file type CDX
*Procedure  1-(Trimethylsilyl)trideca-1,8-diyn-5-yl mesylate (281 mg, 0.80 mmol) in dry DMF (10.0 mL) was added to KCN (146 mg, 2.2 mmol) in dry DMF (5.0 mL).  The reaction mixture was heated to 65 °C for 24 h.  The reaction mixture was poured into water (20 mL) and extracted with ether (3 × 25 mL).  The organic extracts were combined, washed with water (3 × 20 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (241 mg). Purification by column chromatography (SiO2, hexane/Et2O 10:1) gave the title compound as an orange oil (146 mg, 65%).
*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp62.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 94: 2-(4-(Trimethylsilyl)but-3-ynyl)dec-5-yne nitrile

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
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Attached Files
AH Thesis_2011_pp62.pdf
CSRxnsScheme_94.cdx
AH Thesis_2011_pp145-167.pdf