Sodium Methoxide → HCID 18986223, compound

HRID 2396826Notes

Reaction equation

HRID 2396826 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[C:6]([O:14][CH3:15])=[CH:5]1)(=O)C.C[O-].[Na+]>CO>[F:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH:5]=[C:6]2[O:14][CH3:15]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18986212HCID 18986212, compound

Product 1

HCID 18986223HCID 18986223, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.25 g of 1-acetyl-5-fluoro-3-methoxyindole and 0.35 g of sodium methylate in 23 ml of methanol was stirred at room temperature for one hour. After removal of the solvent the residue was extracted with water and ethyl acetate and the organic phase was washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed and the residue was distilled in a bulb-tube at a bath temperature of 200° and a pressure of 50 mbar. 0.76 g (76%) of 5-fluoro-3-methoxyindole was obtained.

Workup

  1. customAfter removal of the solvent the residue
  2. extractionwas extracted with water and ethyl acetate
  3. washthe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. distillationthe residue was distilled in a bulb-tube at a bath temperature of 200°

Sources & evidence

ORD record
ord-9b8dac279b30401db7080874463e9249
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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