Reaktion #4999

Reaktionsgleichung

potassium carbonate

methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoate

methoxyamine hydrochloride

water

→

aimed compound

Ausbeute 60.0%

methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-[1-(N-methoxyimino)ethyl]benzoate

Ausbeute 60.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resultant liquor was heat-refluxed for 3 hours
2. 2
   Sonstigean oily product thus precipitated
3. 3
   Extraktionwas extracted with ethyl acetate
4. 4
   WaschenThe ethyl acetate layer was washed with water
5. 5
   Sonstigewas dried
6. 6
   workup.DISTILLATIONto distill off ethyl acetate under reduced pressure
7. 7
   SonstigeThe residue thus obtained
8. 8
   Sonstigewas purified by chromatography

Vorschrift

1.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoate and 0.5 g of methoxyamine hydrochloride were dissolved in 6 ml of methanol, and the resultant solution was refluxed for 15 minutes. After cooling the mixed liquor to room temperature, 0.8 g of potassium carbonate was added to this liquor and the resultant liquor was heat-refluxed for 3 hours. The reaction liquor was poured into a large amount of water, and an oily product thus precipitated was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and was dried to distill off ethyl acetate under reduced pressure. The residue thus obtained was purified by chromatography to obtain 0.65 g of the aimed compound (refractive index=1.5709) at a yield of 59%.

Quelle