Ethyl 1-oxo-3-phenylindene-2-carboxylate → Ethyl(1RS)-1-Hydroxy-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylate

HRID 862935Notes

Reaction equation

HRID 862935 reaction equation
[O:1]=[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][CH2:20][CH3:21])=[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>[OH:1][C:2]1([C:27]2[CH:26]=[CH:25][C:24]3[O:23][CH2:22][O:30][C:29]=3[CH:28]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:3]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

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

Product 1

HCID 18969644Ethyl(1RS)-1-Hydroxy-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylateYield 72%

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-3fded2dafaa549269661bae8fd2c3503
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

Loading…