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22nd August 2013 @ 08:31

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Reaction information

*#Reaction file  
CSRxnsScheme_74.cdx
*Reaction file type CDX
*Procedure  TMEDA (5.1 mL, 34.0 mmol) and 2-methyl-2-propen-1-ol (1.43 g, 17.0 mmol) were added dropwise sequentially to n-BuLi (13.5 mLof a 2.5 M solution in hexanes, 34.0 mmol) in ether (10.0 mL) at −78 °C.  The reaction mixture was left stirring at room temperature for 15 h.  1-bromooct-3-yne (2.24 g, 12.8 mmol) was added dropwise to the reaction mixture at −78 °C.  The reaction mixture was left stirring at −78 °C for 2 h and at room temperature for 6 h.  The reaction mixture was poured into a sat. aq. NH4Cl solution (100 mL) and extracted with ether (2 × 50 mL).  The organic extracts were combined, washed sequentially with sat. aq. CuSOsolution (3 × 25 mL) and brine (3 × 25 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a colourless oil (1.10 g).  Purification by column chromatography (SiO2, hexane/Et2O 1:1) gave the title compound as a pale yellow oil (898 mg, 42%).
*Yield (%)  42
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp54.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 74: 2-Methylenedec-5-ynol

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Attached Files
CSRxnsScheme_74.cdx
AH Thesis_2011_pp54.pdf
AH Thesis_2011_pp145-167.pdf