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22nd August 2013 @ 08:37

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Reaction information

*#Reaction file  
CSRxnsScheme_71.cdx
*Reaction file type CDX
*Procedure  Diethyl 2-(hept-2-yn-1-yl)malonate  (390 mg, 1.5 mmol) was added dropwise to a stirred suspension of NaH (88.0 mg of a 60% dispersion in mineral oil, 2.2 mmol) in dry THF (14.0 mL).  The reaction mixture was left stirring at room temperature for 1 h.  1-Bromo-2-methylenedec-5-yne  (438 mg, 1.9 mmol) was added dropwise to the reaction mixture at room temperature.  The reaction mixture was left stirring at room temperature for 15 h.  The reaction mixture was poured into a sat. aq. NH4Cl solution (50 mL) and extracted with ether (3 × 30 mL).  The organic extracts were combined, washed with brine (3 × 50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (642 mg).  Purification by column chromatography (SiO2, hexane/Et2O 5:1) gave the title compound as a colourless oil (186 mg, 30%).
*Yield (%)  30
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp52.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 71: Diethyl 2-(hept-2-yn-1-yl)-2-(2-methylenedec-5-yn-1-yl)malonate 

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp52.pdf
CSRxnsScheme_71.cdx
AH Thesis_2011_pp145-167.pdf