Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylate → 1-(3-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650749Notes

Reaction equation

HRID 650749 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](=O)[C:11]=3[C:20]([O:22]CC)=[O:21])=[CH:4][C:3]=2[O:2]1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][CH:32]=1>C1COCC1>[CH3:25][O:26][C:27]1[CH:32]=[C:31]([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]([C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)[CH:11]2[C:20]([OH:22])=[O:21])[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 18427631Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylateHCID 178490745HCID 178490745, compound3×

Product 1

HCID 159085021-(3-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidYield 124.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate (100 mg, 0.31 mmol) in THF (2 ml) under an argon atmosphere at 0° C. was added a solution of freshly prepared 3-methoxyphenyl magnesium bromide (0.31 mmol). After stirring for 15 min, additional 3-methoxyphenyl magnesium bromide (0.06 mmol) was added. Stirring was continued for 45 min, at which time thin layer chromatographic analysis indicated that the reaction was incomplete. Additional 3-methoxyphenyl magnesium bromide (0.12 mmol) was added. After stirring for 2 h more, the mixture was partitioned between 3M HCl and EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 15% EtOAc/hexanes to afford the title compound (150 mg, 100%).

Workup

  1. stirringStirring
  2. waitwas continued for 45 min, at which time thin layer chromatographic analysis
  3. stirringAfter stirring for 2 h more
  4. customthe mixture was partitioned between 3M HCl and EtOAc
  5. extractionThe organic extract
  6. washwas washed successively with H2O, 5% aqueous NaHCO3, H2O and saturated aqueous NaCl
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography
  9. washeluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-c71d19b58d5447f5816cfb9bf6fe4d86
Source dataset
uspto-grants-2001_08
Patent number
US06274737B1

Reaction notes

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