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22nd August 2013 @ 09:15

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Reaction information

*#Reaction file  
CSRxnsScheme_88.cdx
*Reaction file type CDX
*Procedure   Heptadeca-5,12-diyn-9-yl mesylate (904 mg, 2.8 mmol) in dry DMF (8.5 mL) was added to KCN (365 mg, 5.6 mmol).  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 (858 mg). Purification by column chromatography (SiO2, hexane/Et2O 10:1) gave the title compound as an orange oil (468 mg, 65%).
*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp60.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 88: 2-(Oct-3-ynyl)-dec-5-yne nitrile

For multistep reactions (or their steps):

Overall reaction? True
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Attached Files
CSRxnsScheme_88.cdx
AH Thesis_2011_pp60.pdf
AH Thesis_2011_pp145-167.pdf