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21st August 2013 @ 13:45

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Reaction information

*#Reaction file  
CSrxnsScheme_130d.cdx
*Reaction file type CDX
*Procedure

General procedure D (see below) with diene 123c (100 mg, 0.27 mmol) and methyl vinyl ketone (0.04 mL, 0.29 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as a colourless oil (87.0 mg, 72%).

 

General procedure D:

The appropriate dienophile (1.1 eq.) was added to diene 123a,c or j (1 eq.) in benzene (1.00 mL). The reaction mixture was heated at reflux for 16 h. The solvent was removed in vacuo to give the crude product, which was purified as described.

*Yield (%)  72
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp176-223.pdf
AH Thesis_2011_pp100.pdf
Further information  Compound 130d: endo-1-(7-Butyl-1-tosyl-4-(trimethylsilyl)-2,3,4,5,6,7-hexahydro-1H-indol-5-yl)ethanone

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
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Attached Files
AH Thesis_2011_pp100.pdf
CSrxnsScheme_130d.cdx
AH Thesis_2011_pp176-223.pdf