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22nd August 2013 @ 09:01

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Reaction information

*#Reaction file  
CSRxnsScheme_84.cdx
*Reaction file type CDX
*Procedure  Methyl-2-(oct-3-ynyl)dec-5-ynoate (701 mg, 2.4 mmol) was added dropwise to LiAlH4 (137 mg, 3.6 mmol) in dry THF (20 mL).  The reaction mixture was stirred at 0 °C for 30 mins and at room temperature for 2 h.  2 M aq. NaOH solution (2 mL) was added to the reaction mixture.  The reaction mixture was extracted with ether (3 × 50 mL).  The organic extracts were combined, washed with water (2 × 100 mL), dried (MgSO4), filtered and the solvent distilled off under atmospheric pressure to give the crude product as a colourless oil (980 mg). Purification by column chromatography (SiO2, hexane/Et2O 2:1) gave the title compound as a colourless oil (588 mg, 93%).
*Yield (%)  93
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp145-167.pdf
AH Thesis_2011_pp58.pdf
Further information  Compound 84: 2-(Oct-3-ynyl)dec-5-yn-1-ol

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp58.pdf
CSRxnsScheme_84.cdx
AH Thesis_2011_pp145-167.pdf