Reaktion #80277

Reaktionsgleichung

methyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate

sodium hydroxide

water

→

desired compound

Ausbeute 87.0%

5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylic Acid

Ausbeute 87.0%

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with diethyl ether
2. 2
   Sonstigeprecipitated crystals
3. 3
   Extraktionwere extracted with ethyl acetate
4. 4
   Waschenthe organic layer was washed with water
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   EinengenIt was concentrated under reduced pressure
7. 7
   Sonstigethe oily substance thereby obtained
8. 8
   Sonstigewas purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Vorschrift

While stirring 1.2 g of methyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate in 20 ml of dimethylsulfoxide at room temperature, 2 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes and then the mixture was further stirred for 15 hours. The mixture was poured into water and extracted with diethyl ether. Then, the aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate, and the organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 1.0 g (yield: 87%) of the desired compound.

Quelle