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21st August 2013 @ 13:48

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Reaction information

*#Reaction file  
CSRxnsScheme_130e.cdx
*Reaction file type CDX
*Procedure

 General procedure D (see below) with diene 123c (100 mg, 0.27 mmol) and acrolein (0.03 mL, 0.29 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as a yellow oil (93.7 mg, 80%).

 

 

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 (%)  80
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp100.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 130e: endo-7-Butyl-1-tosyl-4-(trimethylsilyl)-2,3,4,5,6,7-hexahydro-1H-indole-5-carbaldehyde

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
AH Thesis_2011_pp100.pdf
CSRxnsScheme_130e.cdx
AH Thesis_2011_pp176-223.pdf