Methyl 7-(6,7-dimethyl-5-hydroxyindan-4-yl)-7-(4-fluorophenyl)heptanoate → 7-(6,7-Dimethyl-5-hydroxy-1-oxoindan-4-yl)-7-(4-fluorophenyl)heptanoic acid

HRID 373389Notes

Reaction equation

HRID 373389 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[C:4]([CH:12]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[C:3]=1[OH:29].[Cr](Cl)([O-])(=O)=[O:31].[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:31])=[C:4]([CH:12]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:3]=1[OH:29]

Participants

4

Reactant 2

HCID 15125109Methyl 7-(6,7-dimethyl-5-hydroxyindan-4-yl)-7-(4-fluorophenyl)heptanoateHCID 178418287HCID 178418287, compound

Product 1

HCID 151251627-(6,7-Dimethyl-5-hydroxy-1-oxoindan-4-yl)-7-(4-fluorophenyl)heptanoic acidYield 28.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of methyl 7-(6,7-dimethyl-5-hydroxyindan-4-yl)-7-(4-fluorophenyl)heptanoate (1.4 g) in benzene (40 ml) was added a mixture of pyridinium chlorochromate (3.8 g) and cerite (7 g) and the mixture was stirred for 2 hours. The reaction mixture was filtered and the filtrate was washed with water and saturated saline and dried with magnesium sulfate. Tetrahydrofuran (10 ml) and 1N sodium hydroxide (10 ml) were added to the residue and the mixture was stirred at room temperature for 13 hours. The solvent was distilled off under reduced pressure and the residue was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from acetonitrile to obtain 7-(6,7-dimethyl-5-hydroxy-1-oxoindan-4-yl)-7-(4-fluorophenyl)heptanoic acid (0.4 g) (Compound 37). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with water and saturated saline
  3. dry with materialdried with magnesium sulfate
  4. additionTetrahydrofuran (10 ml) and 1N sodium hydroxide (10 ml) were added to the residue
  5. stirringthe mixture was stirred at room temperature for 13 hours
  6. distillationThe solvent was distilled off under reduced pressure
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated saline
  9. dry with materialdried with anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-9232e87fedd64ba98d8b98a5cdd2debf
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

Loading…