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21st August 2013 @ 14:07

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Reaction information

*#Reaction file  
*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
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
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Attached Files
AH Thesis_2011_pp110.pdf
AH Thesis_2011_pp224-250.pdf