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22nd August 2013 @ 08:46

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Reaction information

*#Reaction file  
CSRxnsScheme_82.cdx
*Reaction file type CDX
*Procedure  Dimethyl malonate (1.15 mL, 10.0 mmol) was added dropwise to a stirred suspension of NaH (404 mg of a 60% dispersion in mineral oil, 10.1 mmol) in dry DMF (10.0 mL).  The reaction mixture was stirred at room temperature for 1 h.  1-Bromooct-3-yne (2.17 g, 10.1 mmol) was added dropwise to the reaction mixture at room temperature.  The reaction mixture was stirred at room temperature for 30 mins.  NaH (404 mg of a 60% dispersion in mineral oil, 10.1 mmol) was added and the reaction mixture stirred at room temperature for 55 mins. 1-Bromooct-3-yne (2.17 g, 10.1 mmol) was added dropwise to the reaction mixture at room temperature.  The reaction mixture was stirred at 80 °C for 3 h and room temperature for 15 h.  NaH (400 mg of a 60% dispersion in mineral oil, 10.0 mmol) was added to the reaction mixture at room temperature.  The reaction mixture was stirred at room temperature for 1 h.  1-Bromooct-3-yne (2.13 g, 10.0 mmol) was added dropwise to the reaction mixture at room temperature.  The reaction mixture was stirred at 80 °C for 3 h.  Once cool the reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed with brine (2 × 100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a pale yellow oil (4.89 g).  Purification by column chromatography (SiO2, hexane/Et2O 5:1) gave the title compound as a colourless oil (1.40 g, 42%).
*Yield (%)  42
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp58.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 82: Dimethyl-2,2-di(oct-3-ynyl)malonate

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Attached Files
AH Thesis_2011_pp58.pdf
CSRxnsScheme_82.cdx
AH Thesis_2011_pp145-167.pdf