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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 14
63
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Original Articles

The Anion of 4-Dimethoxymethylpyridine. A Convenient Synthesis of Some 4-Pyridyl Ketones A convienient synthesis of some 4-pyridyl ketones

Pages 1967-1971 | Received 22 Feb 1993, Published online: 16 Feb 2007

References

  • Williams , D R , Robinson , L A , Amato , G S and Osterhout , M H . 1992 . J Org Chem , 57 : 3740 For recent examples see
  • Page , P C B , Graham , A E and Park , B K . 1992 . Tetrahedron Letters , 48 : 7265 and references therein.
  • Unpublished observations; these laboratories
  • Taylor , H M and Hauser , C R . Org Syn Coll , Vol 5 437
  • At best a 3:1 mixture in favour of C-alkylation was obtained.
  • Anders , E , Opitz , A and Bauer , W . 1991 . Synthesis , : 1221 The alkylation C versus N of similar anions has been examined:
  • Fieser and Fieser . ‘Reagents for Organic Synthesis’ , Vol 1 993
  • Fuller , M W and Schubert , W M . 1963 . JACS , 85 : 108 The only useful preparation is given by
  • Meyers , A I and Campbell , A L . 1979 . Tetrahedron Letters , : 4155
  • Meyers , A I , Campbell , A L , Abatjoglou , A G and Eliel , E L . 1979 . Tetrahedron Letters , : 4159
  • I am grateful to Prof R A Raphael for suggesting this method of hydrolysis.
  • Other pyridine aldehydes were examined briefly. The acetal of pyridine-3-aldehyde was not expected to behave analogously. That of pyridine-2-aldehyde, although apparently forming an anion on base treatment at -780C gave only intractable mixtures of products when reacted with electrophiles.

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