Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylate → Ethyl (1RS)-1-(4-Fluorophenyl)-1-hydroxy-3-(3,4-methylenedioxyphenyl)indene-2-carboxylate

HRID 399209Notes

Reaction equation

HRID 399209 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.[F:25][C:26]1[CH:31]=[CH:30][C:29]([Mg]Br)=[CH:28][CH:27]=1>C1COCC1>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:12]2([OH:19])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)=[C:11]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 18427631Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylateHCID 178418676HCID 178418676, compound

Product 1

HCID 18969656Ethyl (1RS)-1-(4-Fluorophenyl)-1-hydroxy-3-(3,4-methylenedioxyphenyl)indene-2-carboxylateYield 35%

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 (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-cf95d00449de433ab74fc39732604573
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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