Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylate → Ethyl(1RS)-1-Hydroxy-1-(3-methoxyphenyl)-3-(3,4-methylenedioxypheny)indene-2-carboxylate

HRID 399213Notes

Reaction equation

HRID 399213 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:19])[C:11]=3[C:20]([O:22][CH2:23][CH3:24])=[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>[OH:19][C:12]1([C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([O:26][CH3:25])[CH:32]=2)[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[C:11]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

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

Product 1

HCID 18969638Ethyl(1RS)-1-Hydroxy-1-(3-methoxyphenyl)-3-(3,4-methylenedioxypheny)indene-2-carboxylateYield 112.4%

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-1f442abaf0f844aabcc8321b77fd1ada
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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