Sodium Bicarbonate → HCID 15451894, compound

Participants

Reaction Steps

A mixture of 2-(2-acetoxymethylphenyl)-2-hydroxyiminoacetamide (388 mg, E/Z=35/65) was dissolved in a 5N hydrogen chloride/dioxane solution (3.3 ml), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate three times. The combined ethyl acetate layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (300 mg). This crude product was crystallized from ethyl acetate-hexane, and the crystallization mother liquor was concentrated under reduced pressure and purified by silica gel thin layer chromatography (ethyl acetate:hexane=4:1) to obtain the title compound (243 mg in total, yield: 62.8%, pale yellow crystals).

Provenance & Evidence