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21st August 2013 @ 14:09

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Reaction information

*#Reaction file  
CSRxnsScheme_140.cdx
*Reaction file type CDX
*Procedure  

DIBAL-H (31 mL of a 1.0 m solution in toluene, 31.0 mmol) was added dropwise to a stirred solution of nitrile 148 (2.17 g, 14.7 mmol) in dry THF (45 mL) at ­−78 °C.  The reaction mixture was stirred at ­−78 °C for 30 mins followed by stirring at room temperature for 2 h.  Saturated aq. NaHCO3 solution (100 mL) was added and the reaction mixture stirred at room temperature for 2 h.  The reaction mixture was 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 intermediate aldehyde 149 (2-((1S,6R)-6-vinylcyclohex-3-en-1-yl)acetaldehyde) as a colourless oil (2.13 g).  n-BuLi (8.4 mL of a 2.5 M solution in hexanes, 21.0 mmol) was added dropwise to butyltriphenylphosphonium bromide (8.39 g, 21.0 mmol) in dry THF (60 mL) at 0 °C and left stirring at room temperature for 45 mins.  The reaction mixture was cooled to 0 °C. Intermediate aldehyde 149 (2-((1S,6R)-6-vinylcyclohex-3-en-1-yl)acetaldehyde) (2.11 g, 14.0 mmol) was added dropwise to the reaction mixture at 0 °C and the reaction mixture stirred at room temperature for 45 mins.  The reaction mixture was poured into a sat. aq. NH4Cl solution (300 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with water (200 mL) and brine (200 mL), dried (MgSO4), filtered, concentrated in vacuo, filtered through a plug of silica and the solvent removed in vacuo to give the crude product as a pale yellow oil (4.67 g).  Purification by column chromatography (SiO2, pentane) gave the title compound as a colourless oil (1.64 g, 59% over 2 steps).

*Yield (%)  59
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp110.pdf
AH Thesis_2011_pp224-250.pdf
Further information  Compound 140: (4S,5S)-4-(Hept-2-enyl)-5-vinylcyclohex-1-ene 

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_pp110.pdf
CSRxnsScheme_140.cdx
AH Thesis_2011_pp224-250.pdf