Reaktion #2178396

Reaktionsgleichung

methyl 4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoate

tetrahydrofuran

sodium hydroxide

→

compound

Ausbeute 48.0%

4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid

Ausbeute 48.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith heating
2. 2
   Temperaturunder reflux
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water (40 mL)
5. 5
   workup.ADDITION1N hydrochloric acid (20.0 mL) was added at 0° C
6. 6
   FiltrationThe resulting precipitate was collected by filtration
7. 7
   workup.DISSOLUTIONthe obtained solid was dissolved in ethyl acetate
8. 8
   WaschenThe solution was washed with saturated brine
9. 9
   Trocknendried over magnesium sulfate
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

To a mixture of methyl 4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoate (2.36 g) synthesized above, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20.0 mL), and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (20.0 mL) was added at 0° C. The resulting precipitate was collected by filtration and the obtained solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (1.09 g, 48%) as a pale-red solid.

Quelle