Methanol → HCID 22666525, compound

HRID 1007938Notes

Reaction equation

HRID 1007938 reaction equation
F[C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[CH3:15][OH:16].C[O-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:15][O:16][C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 22666420HCID 22666420, compound

Product 1

HCID 22666525HCID 22666525, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In 35 ml of N,N-dimethylformamide is dissolved 7.00 g of methyl 6-fluorobenzo[b]thiophene-5-carboxylate, to which is added 7.1 mL of a 28% methanol solution of sodium methoxide. The mixture is stirred at 80° C. for 4 hours. Water and ethyl acetate are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: hexane:ethyl acetate=20:1 to 3:1) to obtain 6.30 g of methyl 6-methoxybenzo[b]thiophene-5-carboxylate as an oily product.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customthe residue is purified by column chromatography (eluent: hexane:ethyl acetate=20:1 to 3:1)

Sources & evidence

ORD record
ord-26d3103caea54740b5561c49082aff9c
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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