Sodium Bicarbonate → 4-Methyl-5-propionyloxazole

Reaction equation

CON(C)[C:4]([C:6]1[O:10][CH:9]=[N:8][C:7]=1[CH3:11])=[O:5].[CH2:13]([Mg]Br)[CH3:14].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:11][C:7]1[N:8]=[CH:9][O:10][C:6]=1[C:4](=[O:5])[CH2:13][CH3:14]

Participants

Procedure

N-Methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (5 g) in dry tetrahydrofuran at -40° C. was stirred under a nitrogen atmosphere and ethylmagnesium bromide (1M solution in tetrahydrofuran, 35 ml) was added dropwise. After 30 minutes the mixture was allowed to warm to room temperature and then stirred for a further 1 hour. Aqueous sodium hydrogen carbonate was added, the organic layer was separated and the aqueous layer was extracted with diethylether. The material thus obtained was purified by flash chromatography to yield a pale yellow liquid which solidified on cooling.