HCID 13400171, compound → 7-Methoxy-1-benzofuran-2-carbaldehyde

HRID 2061357Notes

Reaction equation

HRID 2061357 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O)C>C(O)(=O)C>[CH3:16][O:15][C:14]1[C:7]2[O:6][C:5]([CH:4]=[O:3])=[CH:9][C:8]=2[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 13400171HCID 13400171, compound

Product 1

HCID 34573107-Methoxy-1-benzofuran-2-carbaldehydeYield 34.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 28 (2.0 g, 7.46 mmol) in acetic acid (10 mL) was refluxed for 24 h. After cooling, the solution was evaporated to dryness. The crude product was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (4:1) to give 29 (450 mg, 34%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 9.89 (1H, s, CHO), 7.55 (1H, s, ArH), 7.30 (1H, d, J=6.95 Hz, ArH), 7.24 (1H, t, J=7.85, ArH), 6.97 (1H, d, J=6.90 Hz), 4.02 (3H, s, OCH3).

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated to dryness
  3. custompurified by flash chromatography
  4. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-ed7b15980b9449f7bd41886717dc54b4
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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