반응 #1569635

반응 방정식

lithium hydroxide

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

→

title compound

수율 26.0%

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

수율 26.0%

용매

THF

반응 조건

후처리

1. 1
   기타The vial was sealed under nitrogen
2. 2
   온도to cool
3. 3
   기타the volatiles were evaporated under a stream of nitrogen
4. 4
   workup.ADDITIONThe residue was diluted with water (5.0 mL)
5. 5
   추출extracted with EtOAc (3×20 mL)
6. 6
   건조The combined organic extracts were dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The 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
    기타the resulting crude product was further purified by preparative thin layer chromatography (1000 μM thickness, EtOAc)

실험 절차

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.

출처