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22nd August 2013 @ 08:39

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Reaction information

*#Reaction file  
CSRxnsScheme_68.cdx
*Reaction file type CDX
*Procedure  Diethyl 2-(hept-2-yn-1-yl)-2-(2-methylenedec-5-yn-1-yl)malonate (1.69 g, 4.2 mmol) was added dropwise to a stirred suspension of LiAlH4 (512 mg, 13.5 mmol) in dry THF (30 mL) at 0 °C.  The reaction mixture was left stirring at 0°C for 30 mins and at room temperature for 2 h.  2 M aq. NaOH solution was added cautiously until all of the LiAlH4 had been destroyed.  The reaction mixture was extracted with ether (3 × 75 mL).  The organic extracts were combined, washed with water (2 × 200 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude intermediate diol as a colourless oil (1.15 g).  Purification by column chromatography (SiO2, hexane/ethyl acetate 2:1) removed the major impurities to give intermediate diol as a colourless oil (766 mg).  Intermediate diol (741 mg, 2.3 mmol) was added dropwise to a stirred suspension of NaH (448 mg of a 60% dispersion in mineral oil, 11.2 mmol) in dry THF (10.0 mL) at 0°C.  The reaction mixture was left stirring at room temperature for 1 h.  MeI (0.70 mL, 11.2 mmol) was added dropwise to the reaction mixture and left stirring for 3.5 h.  MeOH (5.0 mL) was added dropwise and the reaction mixture extracted with ether (3 × 50 mL).  The organic extracts were combined, washed with brine (2 × 50 mL), dried (MgSO4), filtered and the solvent removed in vacuoto give the crude product as a colourless oil (909 mg).  Purification by column chromatography (SiO2, hexane/ethyl acetate 10:1) gave the title compound as a colourless oil (675 mg, 48% over 2 steps).
*Yield (%)  48
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp52.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 68: 8,8-Bis(methoxymethyl)-10-methyleneoctadeca-5,13-diyne

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp52.pdf
CSRxnsScheme_68.cdx
AH Thesis_2011_pp145-167.pdf