Ethyl 1-oxo-3-phenylindene-2-carboxylate → 1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 650757Notes

Reaction equation

HRID 650757 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]1[C:17]([O:19]CC)=[O:18].[CH2:22]1[O:30][C:29]2[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][C:24]=2[O:23]1>C1COCC1>[CH2:22]1[O:30][C:29]2[CH:28]=[CH:27][C:26]([CH:2]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:3]3[C:17]([OH:19])=[O:18])=[CH:25][C:24]=2[O:23]1

Participants

4

Reactant 2

HCID 18427658Ethyl 1-oxo-3-phenylindene-2-carboxylateHCID 178419615HCID 178419615, compound

Product 1

HCID 217147901-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-oxo-3-phenylindene-2-carboxylate (1.0 g, 3.6 mmol) in THF (35 ml) under an argon atmosphere at 0° C. was added a solution of freshly prepared 3,4-methylenedioxyphenyl magnesium bromide (5.4 mmol). After stirring for 30 min, the mixture was partitioned between 3M HCl and EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 10% EtOAc/ hexanes to afford the title compound (1.03 g, 72%).

Workup

  1. customthe mixture was partitioned between 3M HCl and EtOAc
  2. extractionThe organic extract
  3. washwas washed successively with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography
  7. washeluting with 10% EtOAc/ hexanes

Sources & evidence

ORD record
ord-193ea216bd8e4004954b2d03823bd1f7
Source dataset
uspto-grants-2001_08
Patent number
US06274737B1

Reaction notes

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