Methanol → Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

HRID 1422607Notes

Reaction equation

HRID 1422607 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:11][C:10](=[O:12])[CH2:9][C:6]1[C:5]2[CH:13]=[CH:14][C:2]([OH:1])=[CH:3][C:4]=2[O:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 21109152-(6-Hydroxy-1-benzofuran-3-yl)acetic acid

Product 1

HCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Procedure

A mixture of (6-hydroxy-benzofuran-3-yl)-acetic acid (for preparation see WO 2008001931; 14.0 g), concentrated sulfuric acid (5 mL), and methanol (250 mL) is stirred at reflux temperature for 4 h. After cooling to room temperature, the mixture is concentrated. Ethyl acetate is added to the residue, and the resulting mixture is washed with water, saturated aqueous NaHCO3 solution and brine and dried (MgSO4). The solvent is evaporated, and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1→1:2) to give the title compound. Mass spectrum (ESI+): m/z=207 [M+H]+.

Workup

  1. temperatureat reflux temperature for 4 h
  2. concentrationthe mixture is concentrated
  3. additionEthyl acetate is added to the residue
  4. washthe resulting mixture is washed with water, saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1→1:2)

Sources & evidence

ORD record
ord-6b01b481d85a4d07bc6d3699c2c83fc5
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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