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

HRID 650396Notes

Reaction equation

HRID 650396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[CH:22]=[CH:21][C:20]4[O:23][CH2:24][O:25][C:19]=4[CH:18]=3)=[C:9]2[C:26]([O:28]CC)=[O:27])=[CH:4][CH:3]=1.C1OC2C=CC(C3C4C(=CC=CC=4)C(=O)C=3C(OCC)=O)=CC=2O1.FC1C=CC([Mg]Br)=CC=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[CH:22]=[CH:21][C:20]4[O:23][CH2:24][O:25][C:19]=4[CH:18]=3)[CH:9]2[C:26]([OH:28])=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 18427631Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylateHCID 18969656Ethyl (1RS)-1-(4-Fluorophenyl)-1-hydroxy-3-(3,4-methylenedioxyphenyl)indene-2-carboxylateHCID 178418676HCID 178418676, compound

Product 1

HCID 159085011-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (1RS)-1-(4-Fluorophenyl)-1-hydroxy-3-(3,4-methylenedioxyphenyl)indene-2-carboxylate. To a solution of ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate (100 mg, 0.31 mmol) in THF (5 ml) under an argon atmosphere at 0° C. was added a solution of freshly prepared 4-fluorophenyl magnesium bromide (0.62 mmol). After stirring for 45 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. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 15% EtOAc/hexanes to afford the title compound (45 mg, 35%).

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. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography
  6. washeluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-7e8d00299c8147abb583f19b6c704213
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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