Réaction #80272

Équation de réaction

5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene

potassium permanganate

→

desired compound

Rendement 76.0%

5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methylbenzothiophene -4-carboxylic acid

Rendement 76.0%

Solvants

acetone

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas dropwise added
2. 2
   workup.STIRRINGthe mixture was further stirred at room temperature for 4 hours
3. 3
   ConcentrationIt was then concentrated under reduced pressure
4. 4
   Autreto remove acetone
5. 5
   workup.ADDITIONa saturated sodium bicarbonate aqueous solution was added
6. 6
   ExtractionThe mixture was extracted with ethyl acetate
7. 7
   Autrethe aqueous layer was precipitated with 10% hydrochloric acid
8. 8
   FiltrationThe precipitated crystals were collected by filtration
9. 9
   Lavagewashed with water

Mode opératoire

0.6 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene was dissolved in 80 ml of acetone. While stirring the solution at room temperature, 0.6 g of potassium permanganate dissolved in 10 ml of water was dropwise added thereto over a period of 15 minutes, and the mixture was further stirred at room temperature for 4 hours. It was then concentrated under reduced pressure to remove acetone, and then a saturated sodium bicarbonate aqueous solution was added thereto to make the mixture alkaline. The mixture was extracted with ethyl acetate, and then the aqueous layer was precipitated with 10% hydrochloric acid. The precipitated crystals were collected by filtration and washed with water to obtain 0.47 g (yield: 76%) of the desired compound.

Source