Water → Ethyl 5-methyl-1,3-oxazole-2-carboxylate
Reaction equation
[CH2:1]([NH:5][C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:4])=O.O=P(Cl)(Cl)Cl.O>C1(C)C=CC=CC=1>[CH3:4][C:2]1[O:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][CH:1]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of ethyl 2-(acetonylamino)-2-oxo-acetate (9.2 g, 53.12 mmol) in toluene (100.0 mL), is added POCl3 (4.95 mL, 53.12 mmol) and the reaction mixture is refluxed for 16 hours. The reaction mixture is cooled, added portionwise to water (100.0 mL) and stirred vigorously. The organic layer is washed with saturated NaHCO3 solution (2×50 mL), water (2×50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude material is purified by silica gel chromatography eluting with hexane:ethyl acetate (8.0:2.0) to give the title compound (5.1 g, 61.9%) as a yellow oil. ESI/MS m/z 156.2.1 (M+H)+.