Ethyl (RS)-1,3-Di-(3,4-methylenedioxyphenyl)indene-2-carboxylate → ethyl(1RS,3RS)-1,3-di-(3,4-methylenedioxyphenyl)indane-2-carboxylate

HRID 862933Notes

Reaction equation

HRID 862933 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)=[C:11]3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:4][C:3]=2[O:2]1>CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)[CH:11]3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:4][C:3]=2[O:2]1

Participants

3

Reactant 1

HCID 21714780Ethyl (RS)-1,3-Di-(3,4-methylenedioxyphenyl)indene-2-carboxylate

Product 1

HCID 18969665ethyl(1RS,3RS)-1,3-di-(3,4-methylenedioxyphenyl)indane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl(RS)-1,3-di-(3,4-Methylenedioxyphenyl)indene-2-carboxylate (163 mg, 0.38 mmol) was placed in MeOH (0.05 ml), and to this was added SmI2 (10 ml of 0.1M solution in THF, 1.0 mmol). The resulting mixture was stirred under an argon atmosphere overnight, at which time thin layer chromatographic analysis indicated that the reaction was incomplete. Additional SmI2 (5 ml of 0.1M solution in THF, 0.5 mmol) was added, and stirring was continued for 2 h. The reaction mixture was partitioned between Et2O and 5% aqueous Na2S2O3. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by flash chromatography, eluting with 10% EtOAc/hexanes to afford the title compound as a colorless, glassy solid (120 mg, 75%).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe reaction mixture was partitioned between Et2O and 5% aqueous Na2S2O3
  4. extractionThe organic extract
  5. washwas washed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by flash chromatography
  9. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-0436123adb544ffca0104b2bd8e62868
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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