Sodium Bicarbonate → HCID 54317267, compound

HRID 430766Notes

Reaction equation

HRID 430766 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH:6]1[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])(O)[C:9]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[C:8]=2[O:7]1.C(=O)([O-])O.[Na+]>C1COCC1.C(O)=O>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[O:7][C:8]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:9]=2[C:10]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 53732287HCID 53732287, compound

Product 1

HCID 54317267HCID 54317267, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (2,3-dihydro-2-methoxymethoxymethyl-3-hydroxy-7-methoxybenzofuran-3-yl)acetate (990 mg) was dissolved in THF (25 ml) and formic acid (15 ml), and the obtained solution was stirred at room temperature for 15 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and with saturated brine and dried over magnesium sulfate. Magnesium sulfate was removed by filtration and the solvent was evaporated off. The residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=1/1) to obtain the desired compound (789 mg, yield: 75%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customMagnesium sulfate was removed by filtration
  5. customthe solvent was evaporated off
  6. customThe residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5222dd2919fb4ea58f9d3f8c1584768b
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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