Methanol → Methyl(7-chloro-6-hydroxy-1-benzofuran-3-yl)acetate

HRID 591465Notes

Reaction equation

HRID 591465 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:15].OS(O)(=O)=O.[CH3:21]O>>[CH3:21][O:13][C:12](=[O:14])[CH2:11][C:7]1[C:6]2[CH:5]=[CH:4][C:3]([OH:15])=[C:2]([Cl:1])[C:10]=2[O:9][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 89767735(7-Chloro-6-hydroxy-1-benzofuran-3-yl)acetic acid

Product 1

HCID 119086644Methyl(7-chloro-6-hydroxy-1-benzofuran-3-yl)acetate

Conditions

Temperature
60 °C

Procedure

To a mixture of (7-chloro-6-hydroxy-1-benzofuran-3-yl)acetic acid (1.65 g) and MeOH (40 mL) was added conc. H2SO4 (0.078 mL). The mixture was stirred at 60° C. for 3 h. The mixture was concentrated in vacuo. The residue was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in toluene and hexane. The insoluble material was filtered and washed with toluene and hexane. The filtrate was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.49 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in toluene
  7. filtrationThe insoluble material was filtered
  8. washwashed with toluene and hexane
  9. customThe filtrate was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-7bfd9c1e8294487f9bd6561e1e76daf0
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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