4-Formyloxazole

Abstract

[118994-84-6] C4H3NO2 (MW 97.07) InChI = 1S/C4H3NO2/c6-1-4-2-7-3-5-4/h1-3H InChIKey = JBWIIXBEPINWPB-UHFFFAOYSA-N (electrophilic reagent for incorporation of the 4-oxazolyl unit; aminomalondialdehyde synthetic equivalent) Alternate Names: 4-oxazolecarboxaldehyde; 1,3-oxazole-4-carboxaldehyde. Physical Data: white solid, mp 59–61 °C. Solubility: soluble in most organic solvents such as tetrahydrofuran. Sparingly soluble in water. Handling, Storage, and Precautions: handle and store under inert atmosphere. Incompatible with strong acids and bases, also oxidizing and reducing reagents. No toxicity or hazard data available. Store under nitrogen or argon to prevent oxidation. Form Supplied in: limited commercial availability as a solid. Analysis of Reagent Purity: 1H NMR and elemental analysis (C, H, N). Preparative Methods: can be prepared by partial reduction of ethyl 4-oxazolecarboxylate with diisobutylaluminum hydride in CH2Cl2.1 Alternatively, ethyl 4-oxazolecarboxylate may be reduced to 4-oxazolylmethanol using lithium triethylborohydride, and the alcohol oxidized to 4-formyloxazole by a Swern oxidation.2 Oxazole 4-carboxylic acid may be converted to oxazole 4-carboxylic acid chloride with SOCl2 and the acid chloride reduced to 4-formyloxazole with Pd/BaSO4 and H2.3 Purification: can be recrystallized from CH2Cl2/hexanes.1