Water → Methyl 6-hydroxybenzofuran-3-carboxylate

HRID 556362Notes

Reaction equation

HRID 556362 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 66992646HCID 66992646, compound

Product 1

HCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.9 g (51.4 mMol) 6-Triisopropylsilanyloxy-benzofuran-3-carboxylic acid methyl ester are dissolved in 200 ml DMF. Then 34 g (108 mMol) tetrabutylammoniumfluorid trihydrate are added. After 30 min, the mixture is poured into 400 ml EtOAc and 600 ml water, the aq. phase is separated off and extracted 3 times with EtOAc. The organic layers are washed 4 times with water, brine and dried (Na2SO4). Then char coal is added and the mixture filtered. Partial concentration of the filtrate gives the crystalline title compound, which is filtered off and washed with ether and hexane: m.p.: 200-201° C. More product can be isolated from the filtrate by addition of 280 g SiO2, concentration, application to a chromatography column (SiO2; hexane/EtOAc 3: 1) and eluation with hexane/EtOAc 3:1.

Workup

  1. customthe aq. phase is separated off
  2. extractionextracted 3 times with EtOAc
  3. washThe organic layers are washed 4 times with water, brine
  4. dry with materialdried (Na2SO4)
  5. additionThen char coal is added
  6. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-3a4947bc2e844260a6ca3ce3fe210ca1
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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