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Is it possible to convert Alkoxide to tosylate directly?



Need help:

  J. of Labelled Compounds and Radiopharmaceuticals(34(4), 383-90; 
1994) reported a method for preparation HOCH2CH2OH (Carbon 11 labeled)
from KCN (C11) in three steps
  Step 1: KCN + ClCH2OC(O)C(CH3)3 ----> CNCH2OC(O)C(CH3)3
  Step 2: CNCH2OC(O)C(CH3)3 +HCl +EtOH ---> HOCH2CO2Et
  Step 3: HOCH2CO2Et + LiAlH4 ----> HOCH2CH2OH 
  

  Now I need to prepare labeled TsOCH2CH2OTs. However workup in step 3
is a tedious process since it is quite difficult to seperate
HOCH2CH2OH from water and Al(OH)3. My question is: can I add pTsCl to
the step 3 raction mixture to make TsOCH2CH2OTs directly from
-Al-OCH2CH2O-Al-?  Do anyone has such experience or know some
reference about it?

Thanks

Jason
-- 
Paul J. Franklin(moderator - sci.chem.organic.synthesis) 
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <[EMAIL PROTECTED]>
Atlanta, GA



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