Transformation of Amides to Esters

[java]

Transformation of Amides into Esters by the Use of Chlorotrimethylsilane

Abstract   A mild transforma tion of various amides and imides into the corresponding esters and diesters in good yields by using chlorotrimethylsilane and alcohols that are described. Either primary, secondary, or tertiary amide or imide can be used in this transformation. Primary and secondary alcohols gave better yields than tertiary alcohols.

Journal of Chinese Chemical Society, 51,359-362-,2004
Cuihua Xue  and Fen-Tair Luoa,

http://nr.stic.gov.tw/ejournal/ChiChemSociety/2004/EJ52-2004-359.pdf


Narrative The mild conversion of amides into esters by the use of acidic resins has been reported. 11 However, this process is specific for unsubstituted carboxamides. Thus, a new approach is still needed for this conversion. Herein, we report the scope of the transformation  of various amides and imides into esters or diesters in good yields by a convenient approach.....



Conclusion..... we have found a very mild and general method for the preparation of esters from amide in good to excellent yields by using two equiv of primary or secondary alcohols and the in situ generated HCl from chlorotrimethylsilane at room temperature.


Ref.
11. Greenlee, W. J.; Thorsett, E. D.  J. Org. Chem. 1981, 26, 5351.

[archivist]

Sorry for the ignorance Java- but Swim doesn't get it.  What does this have to do with the "chemistry of mind-altering compounds"? Isn't the point to go in the other direction?