Potassium Carbonate → 2-(n-Propoxyimino)acetoacetic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3](=[O:10])[C:4](=[N:8][OH:9])[C:5]([CH3:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH2:18][CH3:19]>CC(C)=O>[CH3:1][O:2][C:3](=[O:10])[C:4](=[N:8][O:9][CH2:17][CH2:18][CH3:19])[C:5]([CH3:7])=[O:6]

Participants

Procedure

To a solution of 13.6 g of 2-hydroxyiminoacetoacetic acid methyl ester in 70 ml of acetone is added under ice cooling 20.8 g of potassium carbonate. To the mixture is added dropwise 17.0 g of n-propyl iodide in the course of 30 minutes. At the end of the dropwise addition, the mixture is stirred at room temperature for 2 hours. Acetone is evaporated under reduced pressure. To the residue is added 250 ml of water, and the mixture is subjected to extraction with methylene chloride. The extract is washed with water twice, dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to yield 2-(n-propoxyimino)acetoacetic acid methyl ester as a pale yellow oily product.