FORMYLATION OF 2,5-UNSUBSTITUTED OXAZOLE - PREPARATION AND CHARACTERIZATION OF 2 AND 5-FORMYL-4-METHYLOXAZOLES

Authors
SINDLERKULYK M VOJNOVIC D DEFTERDAROVIC N MARINIC Z SRZIC D
Citation
M. Sindlerkulyk et al., FORMYLATION OF 2,5-UNSUBSTITUTED OXAZOLE - PREPARATION AND CHARACTERIZATION OF 2 AND 5-FORMYL-4-METHYLOXAZOLES, Heterocycles, 38(8), 1994, pp. 1791-1796
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
8
Year of publication
1994
Pages
1791 - 1796
Database
ISI
SICI code
0385-5414(1994)38:8<1791:FO2O-P>2.0.ZU;2-4
Abstract
Vilsmeier formylation of 4-methyloxazole (1) gave a mixture of 4-methy l-5-oxazolecarboxaldehyde (2) and 4-methyl-2-oxazolecarboxaldehyde (3) in 1:1 ratio. Both aldehydes were prepared unambiguously: aldehyde (2 ) by oxidation of 5-hydroxymethyl-4-methyloxazole (4) and reduction of chloride of 4-methyl-5-oxazolecarboxylic acid (5) and aldehyde (3) by n-butyllithium/DME procedure. Aldehyde (2) sublimes in a refrigerator while aldehyde (3) forms hydrate, 5-dihydroxymethyl-4-methyloxazole ( 8).