1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole → 1-(3-Hydroxybenzyl)-5-methoxy-2-phenylindole

HRID 1191651Notes

Reaction equation

HRID 1191651 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.O.CSC>[OH:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 696710521-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole

Product 1

HCID 696709171-(3-Hydroxybenzyl)-5-methoxy-2-phenylindoleYield 70%

Reagents, catalysts & solvents 1

HCID 86597598Trifluoroacetic acid water dimethylsulfideSolvent

Procedure

1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole (200 mg) was dissolved in trifluoroacetic acid-water-dimethyl sulfide (95/5/10, 4.8 mL), and the solution was stirred at room temperature for 68 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (110 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-017956df7c7b4e1596a409f3717b2702
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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