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21st August 2013 @ 14:37

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Reaction information

*#Reaction file  
CSRxnsScheme_176.cdx
*Reaction file type CDX
*Procedure  Diazomethane in dry ether [produced by addition of KOH (99.0 mg, 1.9 mmol) in 96% ethanol (4.0 mL) to Diazald® (107 mg, 0.50 mmol) in dry ether (14.0 mL)] was distilled into a flask containing acid 139 (40.0 mg, 0.13 mmol) in ether (1.00 mL) at −78 °C.  The reaction mixture was stirred at −78 °C for 20 mins followed by stirring at room temperature for 1 h to remove excess diazomethane.  The solvent was removed in vacuo to give a pale yellow oil (112 mg).  Purification by column chromatography (SiO2, hexane/Et2O 20:1) gave the title compound as a colourless oil (37.5 mg, 91%).
*Yield (%)  91
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp123.pdf
AH Thesis_2011_pp224-250.pdf
Further information  Compound 176: (E)-Methyl 7-((1R,2S,3aR,7aR)-2-butyl-2,3,3a,4,7,7a-hexahydro-1H-inden-1-yl)hept-5-enoate

For multistep reactions (or their steps):

Overall reaction? True
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Attached Files
AH Thesis_2011_pp123.pdf
CSRxnsScheme_176.cdx
AH Thesis_2011_pp224-250.pdf