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

HRID 273333Notes

Reaction equation

HRID 273333 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:8][O:9][C:5]=2[CH:4]=1.OS(O)(=O)=O.[CH3:21]O>>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][C:11]([O:13][CH3:21])=[O:12])=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7368182-(6-Methoxy-1-benzofuran-3-yl)acetic acid

Product 1

HCID 15618717Methyl 2-(6-methoxy-1-benzofuran-3-yl)acetateYield 98%

Procedure

A mixture of (6-methoxy-benzofuran-3-yl)-acetic acid (2 g, 9.7 mmol) and H2SO4 (0.3 mL) in methanol (40 mL) was refluxed for 8 h and then concentrated. An aqueous NaHCO3 solution was added, followed by extraction with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and evaporated to give a brown oil, which was purified on a silica gel column eluting with EtOAc/hexane (1:10) to give methyl 2-(6-methoxybenzofuran-3-yl)acetate (2.1 g, 98%)

Workup

  1. temperaturewas refluxed for 8 h
  2. concentrationconcentrated
  3. additionAn aqueous NaHCO3 solution was added
  4. extractionfollowed by extraction with CH2Cl2
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customevaporated
  7. customto give a brown oil, which
  8. customwas purified on a silica gel column
  9. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-a6400cd7904f4f4a9f4a7843eedce52e
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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