Synthesis of desyl esters by the application of phase transfer catalysis and a study of the fluorescent properties of 2-substituted i,5-diphenyloxazoles derived from desyl esters

Abstract

Desyl alcohol was converted to desyi chloride by the application of phasetransfer catalysis using triethyl benzyl ammonium chloride (TEBA) in aqueous sodium hydroxide and chloroform at 0–5° C. The desyl chloride thus obtained was condensed with the potassium salts of various carboxylic acids under phase-transfer catalysis using PEG-400 to give the desyl esters in excellent yields. These were cyclized to 2-substituted4,5-diphenyloxazoles. 2-(4-Nitrophenyl)-4,5-diphenyloxazole was reduced to the 2-(4-aminophenyl) derivative, which upon acetylation yielded 2-(4-acetamidophenyl)-4,5-diphenyloxazole. The fluorescent properties of the 2-substituted 4,5-diphenyloxazoles were studied.