Reaktion #1569635

Reaktionsgleichung

lithium hydroxide

methyl 7-methoxy-2-(4-(methoxycarbonyl)benzyl)-1-oxo-4-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-2-carboxylate

→

title compound

Ausbeute 26.0%

4-((7-Methoxy-1-oxo-4-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-2-yl)methyl)benzoic acid

Ausbeute 26.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was sealed under nitrogen
2. 2
   Temperaturto cool
3. 3
   Sonstigethe volatiles were evaporated under a stream of nitrogen
4. 4
   workup.ADDITIONThe residue was diluted with water (5.0 mL)
5. 5
   Extraktionextracted with EtOAc (3×20 mL)
6. 6
   TrocknenThe combined organic extracts were dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe resulting crude residue was purified by combiflash (4 g column, CH2Cl2→20% MeOH/CH2Cl2, gradient)
10. 10
    workup.ADDITIONAll fractions containing the desired product
11. 11
    Sonstigethe resulting crude product was further purified by preparative thin layer chromatography (1000 μM thickness, EtOAc)

Vorschrift

Aqueous lithium hydroxide (1 N, 1.0 mL, 1.0 mmol) was added to a solution of methyl 7-methoxy-2-(4-(methoxycarbonyl)benzyl)-1-oxo-4-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-2-carboxylate (36 mg, 0.071 mmol) in THF (1.0 mL) in a scintillation vial. The vial was sealed under nitrogen and heated at 60° C. After 24 h, the reaction mixture was allowed to cool and the volatiles were evaporated under a stream of nitrogen. The residue was diluted with water (5.0 mL), acidified with 1 N aqueous HCl (2.0 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude residue was purified by combiflash (4 g column, CH2Cl2→20% MeOH/CH2Cl2, gradient). All fractions containing the desired product were combined and the resulting crude product was further purified by preparative thin layer chromatography (1000 μM thickness, EtOAc), to afford 8 mg (26%) of the title compound.

Quelle