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22nd August 2013 @ 09:34

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Reaction information

*#Reaction file  
CSRxnsScheme_92.cdx
*Reaction file type CDX
*Procedure  Magnesium turnings (608 mg, 25.0 mmol) were ground in a mortar and pestle followed by vigorous stirring under argon overnight.  The stirring was stopped, dry THF (1.0 mL) and iodine (1 crystal) were added.  1-Bromooct-3-yne  (759 mg, 4.0 mmol), 1,2-dibromoethane (0.43 mL, 5.0 mmol) and dry THF (4.0 mL) were combined.  Approximately 10% of the 1‑bromooct‑3‑yne containing mixture was added to the magnesium turnings.  Once bubbling had started the remainder of the mixture containing 1-Bromooct-3-yne  was added slowly to maintain a gentle reflux.  The reaction mixture was heated to reflux for 2 h.  The Grignard formed was added dropwise to a solution of 5‑(trimethylsilyl)pent-4-ynal (694 mg, 5.0 mmol) in dry THF (20 mL) at 0 °C. After stirring at room temperature for 3 h the reaction mixture was poured into a sat. aq. NH4Cl solution (20 mL) and extracted with ether (3 × 10 mL).  The organic extracts were combined washed with water (2 × 20 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (1.49 g). Purification by column chromatography (SiO2, hexane/Et2O 3:1) gave the title compound as an orange oil (330 mg, 31%).
*Yield (%)  31
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp62.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 92: 1-(Trimethylsilyl)trideca-1,8-diyn-5-ol

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Attached Files
CSRxnsScheme_92.cdx
AH Thesis_2011_pp62.pdf
AH Thesis_2011_pp145-167.pdf