HCID 59603127, compound → 2-Benzofurancarboxaldehyde, 5-methoxy-

HRID 2061353Notes

Reaction equation

HRID 2061353 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=1[CH:9]=O)C>C(O)(=O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:7]2[O:6][C:5]([CH:4]=[O:3])=[CH:9][C:8]=2[CH:11]=1

Participants

3

Reactant 1

HCID 59603127HCID 59603127, compound

Product 1

HCID 316632-Benzofurancarboxaldehyde, 5-methoxy-Yield 24.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 23 (1.0 g, 3.74 mmol) in acetic acid (10 mL) was refluxed for 16 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 24 (160 mg, 24%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 9.80 (1H, s, CHO), 7.49-7.45 (2H, m, ArH), 7.12-7.09 (2H, m, ArH), 3.85 (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-eaf5497ef6ac4bfe83e53c766189ef89
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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