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21st August 2013 @ 14:07

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Reaction information

*#Reaction file  
CSRxnsScheme_148.cdx
*Reaction file type CDX
*Procedure  A solution of mesylate 147 (3.91 g, 18.1 mmol) and 18‑crown‑6 (2.59 g, 9.8 mmol) in dry MeCN (65 mL) was added to KCN (2.36 g, 36.2 mmol) and NaI (195 mg, 1.3 mmol).  The reaction mixture was heated to reflux for 60 h.  After cooling to room temperature the reaction mixture was poured into water (200 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed with brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (2.80 g).  Purification by column chromatography (SiO2, hexane/Et2O 5:1) gave the title compound as a colourless oil (2.25 g, 84%).
*Yield (%)  84
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp224-250.pdf
AH Thesis_2011_pp110.pdf
Further information  Compound 148: 2-((1R,6S)-6-Vinylcyclohex-3-enyl)acetonitrile

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
CSRxnsScheme_148.cdx
AH Thesis_2011_pp110.pdf
AH Thesis_2011_pp224-250.pdf