Reaktion #477850

Reaktionsgleichung

sodium hydroxide

ethyl 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate

→

2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyric acid

Ausbeute 76.0%

Lösungsmittel

ethanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction medium is evaporated to dryness
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Waschenwashed with water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   FiltrationAfter filtration
6. 6
   Sonstigethe solvent is evaporated off
7. 7
   Sonstigethe oil obtained
8. 8
   Sonstigeis purified by chromatography on a column of silica
9. 9
   Wascheneluted with a 60/40 heptane/ethyl acetate mixture
10. 10
    Sonstigeprecipitated from heptane

Vorschrift

40 mg (1 mmol) of sodium hydroxide are added to a solution of 531 mg (1 mmol) of ethyl 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate in 1 mL of ethanol and 10 mL of tetrahydrofuran. The reaction mixture is heated at 50° C. for 48 hours. The reaction medium is evaporated to dryness, taken up in water, acidified with aqueous 2 N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. After filtration, the solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture and then precipitated from heptane. 317 mg (76%) of 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyric acid are obtained in the form of a white powder with a melting point of 62-64° C.

Quelle