5-Chloro-2-(2,2-diethoxyethoxy)benzaldehyde → 5-Chloro-1-benzofuran-2-carbaldehyde

HRID 2061360Notes

Reaction equation

HRID 2061360 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([O:16]CC)OCC)=[C:6]([CH:9]=1)[CH:7]=O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:11]([CH:12]=[O:16])=[CH:7][C:6]=2[CH:9]=1

Participants

3

Reactant 1

HCID 596031345-Chloro-2-(2,2-diethoxyethoxy)benzaldehyde

Product 1

HCID 134001705-Chloro-1-benzofuran-2-carbaldehydeYield 20.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 33 (4.10 g, 15.07 mmol) in acetic acid (20 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 34 (550 mg, 20%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 9.91 (1H, s, CHO), 7.76 (1H, d, J=1.85 Hz, ArH), 7.57 (1H, d, J=8.90 Hz, ArH), 7.53 (1H, s, ArH), 7.50 (1H, dd, J=8.90 & 2.10 Hz, ArH).

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-90fa7bfa7baf40229e6011ccd34d187d
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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