Diethyl [(2-methyl-4-phenyl-1,3-oxazol-5-yl)methyl]propanedioate → 3-(2-Methyl-4-phenyl-1,3-oxazol-5-yl)propanoic acid

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Reaction Steps

Diethyl 2-(2-methyl-4-phenyl-5-oxazolylmethyl)malonate (8.0 g) was dissolved in a mixture of acetic acid (50 ml) and 6N hydrochloric acid (20 ml) and the solution was refluxed with stirring for 3 hours. The solvent was then distilled off and the residue was made alkaline with 2N sodium hydroxide and washed with ethyl ether. The alkaline solution was adjusted to pH 2 with concentrated hydrochloric acid to give 2-methyl-4-phenyloxazole-5-propionic acid as crystals, yield 4.85 g (overall yield from the 5-bromomethyl compound=57.5%). Recrystallization from ethanol gave colorless prisms, yield 3.40 g (overall yield from the bromomethyl compound=40.3%), m.p. 156°-157° C.

Provenance & Evidence