1-(6-Methoxy-benzofuran-3-yl)-ethane-1,2-diol → 6-Methoxybenzofuran-3-carbaldehyde

HRID 273336Notes

Reaction equation

HRID 273336 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH:10]([OH:13])CO)=[CH:8][O:9][C:5]=2[CH:4]=1>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH:10]=[O:13])=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 691973081-(6-Methoxy-benzofuran-3-yl)-ethane-1,2-diol

Product 1

HCID 824109866-Methoxybenzofuran-3-carbaldehydeYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

NaIO4 (0.204 g, 1.12 mmol) was added to 1-(6-methoxy-benzofuran-3-yl)-ethane-1,2-diol (0.180 g, 1.196 mmol) in THF (50 mL) and water (1 mL) with stirring. The mixture was stirred overnight at room temperature under N2. Water (10 mL) was added, and the mixture was concentrated to half its volume and extracted with EtOAc. The organic layer was washed with brine and water, dried over anhyd. MgSO4, and evaporated to give a residue, which was purified on a silica gel column eluting with EtOAc/hexane (1:10) to give 6-methoxybenzofuran-3-carbaldehyde (0.110 g, 73%).

Workup

  1. stirringThe mixture was stirred overnight at room temperature under N2
  2. concentrationthe mixture was concentrated to half its volume
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine and water
  5. customdried over anhyd
  6. customMgSO4, and evaporated
  7. customto give a residue, which
  8. customwas purified on a silica gel column
  9. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-48aeedf470cd4b08826f5be8112c6084
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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