Ethyl 5-methoxy-3-methyl-1-benzofuran-2-carboxylate → Ethyl 5-hydroxy-3-methyl-1-benzofuran-2-carboxylate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe mixture was heated