120224-25-1Relevant articles and documents
A CONVENIENT PREPARATION OF 3H-1,3-OXAZOL-2-ONE AND ITS N-FORMYL DERIVATIVE
Tavernier, Dirk,Damme, Sabine van,Ricquier, Patrick,Anteunis, Marc J. O.
, p. 859 - 866 (2007/10/02)
The electrochemical hydroxylation of 1,3-oxazolidin-2-one to 4-hydroxy-1,3-oxazolidin-2-one is reported; a substantial size product is the symmetrical ether derived from the hydroxycompound.An improved synthesis of 3H-1,3-oxazol-2-one has been developed; nothing more is involved than boiling the readily available 4-methoxy-1,3-oxazolidin-2-one with an excess of acetic acid and one equivalent of acetic anhydride, evaporation of the solvents and recrystallization of the residue.The mechanism of the reaction is discussed.In a reinvestigation of the known conversion, by acetic anhydride, of 4-methoxy-1,3-oxazolidin-2-one to N-acetyl-1,3-oxazol-2-one, we have uncovered the formation of two 3,4'-bioxazole side products , especially in the presence of added acids.We have found that N-formyl-1,3-oxazol-2-one can be made in good yield by treatment of 3H-1,3-oxazol-2-one with a mixture of formic acid and acetic anhydride ("acetic formic anhydride") in the presence of 4-(N,N-dimethylamino)pyridine; the formation of an intermediate phosphonate derived from 3H-1,3-oxazol-2-one, as described in the literature synthesis of N-formyl-1,3-oxazolone, is superfluous.
