Lithium Hydroxide → HCID 86279503, compound

HRID 2170742Notes

Reaction equation

HRID 2170742 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)=[C:9]2[C:13]=1[C:12](=[O:14])[C:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=1)(C(OC)=O)[CH2:10]2>C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:39])[F:38])[CH:31]=2)=[C:9]2[C:13]=1[C:12](=[O:14])[CH:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][CH:21]=1)[CH2:10]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117665502HCID 117665502, compound

Product 1

HCID 86279503HCID 86279503, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  1. customThe vial was sealed under nitrogen
  2. temperatureto cool
  3. customthe volatiles were evaporated under a stream of nitrogen
  4. additionThe residue was diluted with water (5.0 mL)
  5. extractionextracted with EtOAc (3×20 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting crude residue was purified by combiflash (4 g column, CH2Cl2→20% MeOH/CH2Cl2, gradient)
  10. additionAll fractions containing the desired product
  11. customthe resulting crude product was further purified by preparative thin layer chromatography (1000 μM thickness, EtOAc)

Sources & evidence

ORD record
ord-efbea74d2a1642abab88eda2d40ca214
Source dataset
uspto-grants-2015_06
Patent number
US09051294B2

Reaction notes

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