2-hydroxy-5-methyl-N-(2-methoxycarbonylbenzylidene)aniline → Methyl 2-(5-methylbenzoxazol-2-yl)benzoate

Participants

Reaction Steps

Lead tetraacetate (16.6 g) was added portionwise to a solution of compound B (8.1 g) in chloroform (150 ml) and the mixture was stirred for 2 hours. Insoluble material was removed by filtration and the filtrate was washed with water (3×50 ml), followed by saturated sodium chloride solution (50 ml), and then dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:9 v/v), to give methyl 2-(5-methylbenzoxazol-2-yl)benzoate (C) (5.2 g), as an oil; NMR: 2.5(s, 3H), 3.85(s, 3H), 7.2(dd, 1H), 7.45(d, 1H), 7.55-7.7(m, 3H), 7.75-7.8(m, 1H), 8.05-8.1(m, 1H).

Provenance & Evidence