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22nd August 2013 @ 09:49

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Reaction information

*#Reaction file  
CSRxnsScheme_90.cdx
*Reaction file type CDX
*Procedure  DIBAL-H (2.6 mL of a 1.0 M solution in THF, 2.6 mmol) was added dropwise to a solution of 2-(4-(Trimethylsilyl)but-3-ynyl)dec-5-yne nitrile (349 mg, 1.3 mmol) in dry THF (4.0 mL) at −78 °C.  The reaction mixture was stirred at ­−78 °C for 15 mins and at room temperature for 2 h.  Ethyl acetate (5.0 mL) was added followed by a sat. aq. solution of Rochelle salt  (15.0 mL) and stirring was continued for 30 mins.  The reaction mixture was extracted with ether (3 × 20 mL).  The organic extracts were combined, washed with brine (2 × 25 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude intermediate aldehyde as a colourless oil (345 mg).  n-BuLi (0.96 mL of a 2.5 M solution in hexanes, 2.4 mmol) was added dropwise to methyltriphenylphosphonium bromide (874 mg, 2.4 mmol) in dry THF (5.0 mL) at −20 °C and left stirring at this temperature for 30 mins. Intermediate aldehyde  (338 mg, 1.2 mmol) was added dropwise to the reaction mixture at −78 °C and the reaction mixture stirred at this temperature for 30 mins.  The reaction mixture was then stirred at room temperature for 90 mins, poured into a cold sat. aq. NH4Cl solution (50 mL) and extracted with ether (3 × 30 mL).  The organic extracts were combined, washed with brine (2 × 40 mL), dried (MgSO4), filtered, concentrated in vacuofiltered through a plug of silica and the solvent removed in vacuo to give the crude product as a pale yellow oil (302 mg). Purification by column chromatography (SiO2, hexane/Et2O 30:1) gave the title compound as a colourless oil (106 mg, 31% over 2 steps).
*Yield (%)  31
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp62.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 90: Trimethyl(5-vinyltrideca-1,8-diynyl)silane

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Attached Files
CSRxnsScheme_90.cdx
AH Thesis_2011_pp62.pdf
AH Thesis_2011_pp145-167.pdf