Water → 6-(4-methoxyphenyl)-1H-indole

HRID 2210599Notes

Reaction equation

HRID 2210599 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][N:15]3C(OC(C)(C)C)=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].C(Cl)Cl.O>CO.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][NH:15]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 112095106-(4-Methoxyphenyl)-1-tert-butoxycarbonylindole

Product 1

HCID 152927466-(4-methoxyphenyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 6-(4-methoxyphenyl)-1-tert-butoxycarbonylindole (3.9 g, 12 mmol) in methanol (50 mL) was added 1N methanolic NaOH (60 mL) and CH2Cl2 (20 mL). The reaction was stirred for one hour at ambient temperature and 1.5 hours at reflux. The reaction mixture was cooled to ambient temperature and H2O (50 mL) was added to dissolve all solids. The two-phase mixture was poured into CHCl3 and the layers where separated. The organic phase was washed with brine, dired over MgSO4, filtered, and concentrated in vacuo. Flash chromatography on silica gel (100 g, 25% ethyl acetate, hexanes) afforded 6-(4-methoxyphenyl)indole as white flakes (2.2 g, 81%).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. dissolutionto dissolve all solids
  4. customthe layers where separated
  5. washThe organic phase was washed with brine
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff4be33230f040a0969b687ef15a0dd8
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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