Sodium Hydroxide → HCID 67086769, compound

HRID 1665184Notes

Reaction equation

HRID 1665184 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][CH2:15][O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].[OH-].[Na+]>CO>[CH3:22][O:21][CH2:20][CH2:19][O:18][CH2:17][O:16][CH2:15][CH2:14][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=2[CH:7]=[CH:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67087130HCID 67087130, compound

Product 1

HCID 67086769HCID 67086769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2-(2-Methoxy-ethoxymethoxy)-ethyl]-1H-indole-4-carboxylic acid methyl ester (69 mg, 0.225 mmol) in MeOH (2 ml) is added 2 M NaOH (1 ml) and the reaction is stirred at room temperature for 19.5 hours, then for 2 hours at 50° C. The reaction is allowed to cool to room temperature and the solvent removed in vacuo. To the residue is added sat. NH4Cl (10 ml), and the product is extracted with EtOAc (5×25 ml), washed with brine (10 ml), dried over Na2SO4, and the solvent is removed in vacuo, to give the title compound 1-[2-(2-Methoxy-ethoxymethoxy)-ethyl]-1H-indole-4-carboxylic acid; [M+H]+ 294

Workup

  1. waitfor 2 hours at 50° C
  2. temperatureto cool to room temperature
  3. customthe solvent removed in vacuo
  4. additionTo the residue is added sat. NH4Cl (10 ml)
  5. extractionthe product is extracted with EtOAc (5×25 ml)
  6. washwashed with brine (10 ml)
  7. dry with materialdried over Na2SO4
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-656af2454a004e8b90ba86d6bbead72d
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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