Water → HCID 71278662, compound

HRID 1749909Notes

Reaction equation

HRID 1749909 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[C:12]([OH:14])=O.[C:15](=O)([O-])[O-].[K+].[K+].S([O:26][CH3:27])(OC)(=O)=O.O>CN(C=O)C>[CH3:15][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[C:12]([O:26][CH3:27])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86682036HCID 86682036, compound

Product 1

HCID 71278662HCID 71278662, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid (0.30 g, 1.6 mmol) in DMF (10 mL) was added with potassium carbonate (0.63 g, 4.6 mmol) and dimethyl sulfate (0.48 g, 3.8 mmol), and the mixture was stirred at room temperature for 1 hour, and at 40° C. for 3 hours. The reaction mixture was added with water, the mixture was extracted with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain methyl 6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylate (0.25 g, 71%).

Workup

  1. waitat 40° C. for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-98405c89bec34ba3806b04eea361221e
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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