Ethyl 5-methoxy-3-methyl-1-benzofuran-2-carboxylate → Ethyl 5-hydroxy-3-methyl-1-benzofuran-2-carboxylate

HRID 606582Notes

Reaction equation

HRID 606582 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11]C)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]>ClCCl>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

3

Reactant 1

HCID 2307798Ethyl 5-methoxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 42883413Ethyl 5-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 3-methyl-5-methoxybenzofuran carboxylate (8.53 mmol) was dissolved in dichloromethane (10 ml) and a 1.0 M solution of boron tribromide methyl sulphide complex in dichloromethane (25.59 mmol) was added. The mixture was heated at reflux over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 3-methyl-5-hydroxybenzofuran carboxylate as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux over night
  3. customThe solvent was evaporated under vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-6ebdd579a1994699bfb77be6cea168e5
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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