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16th September 2013 @ 13:50

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Reaction information

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

To a stirred solution of tert-butyl 2-(3-((3aR,6aS)-2-hexyl-6a-(1-phenylvinyl)-3,3a,4,5,6,6a-hexahydropentalen-1-yl)propoxy)acetate (43 mg, 0.09 mmol) in DCM (0.8 mL) was added TFA (0.2 mL) dropwise.  The reaction was stirred for 1 hour.  TLC showed some of the SM still remained so extra TFA (0.2 mL) was added and the reaction was stirred for 30 min.  TLC showed no SM remained.

The reaction mixture was concentrated under reduced pressure and redissolved in chloroform before being concentrated again (a process that was repeated 3 times).  Due to the presence of the impurity from the starting material, the product was purified by column chromatography (silica gel, 5 % methanol in DCM, then 50 % methanol in DCM) to give the pure product (37 mg, 0.09 mmol, 98 %). 

*Yield (%) 98
*Type of Yield Isolated Product Yield
Reference(s)
L.Sayerpp35.pdf
 
Further information

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step Reaction 64 
For step in multistep reaction - link to following reaction step N/A 
Attached Files
ReactionScheme.cdx
L.Sayerpp35.pdf