Phosphorus oxychloride → 4-Benzyloxy-benzofuran-7-carbaldehyde

HRID 479194Notes

Reaction equation

HRID 479194 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14]1[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:23]([O-])(=[O:25])C.[Na+]>CN(C)C=O>[CH2:6]([O:13][C:14]1[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]([CH:23]=[O:25])=[CH:16][CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 226475654-Benzyloxy-benzofuran

Product 1

HCID 226476054-Benzyloxy-benzofuran-7-carbaldehydeYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

Dry N,N-dimethylformamide (12.1 g, 166 mmol) was added dropwise with stirring and cooling under an argon atmosphere to phosphorous oxychloride (11.4 g, 75 mmol) at such a rate that the temperature did not exceed 10° C. After 30 min at 10° C., a solution of 4-benzyloxy-benzofuran (9.3 g, 41 mmol) in N,N-dimethylformamide (9 ml) was added dropwise within 30 min. The reaction mixture was stirred 30 min at ambient temperature and then continuously heated to 100° C. After 10 min at 100° C. the mixture was heated at 85° C. for 3 h, cooled to 10° C., neutralized with 25% aqueous sodium acetate, with cooling, and extracted with diethyl ether. The extract was washed with saturated aqueous sodium bicarbonate and water and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, hexane/AcOEt=19/1) to give 1.8 g (7 mmol, 17%) of the title compound as yellow oil.

Workup

  1. customdid not exceed 10° C
  2. stirringThe reaction mixture was stirred 30 min at ambient temperature
  3. temperatureAfter 10 min at 100° C. the mixture was heated at 85° C. for 3 h
  4. temperaturecooled to 10° C.
  5. temperaturewith cooling
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with saturated aqueous sodium bicarbonate and water
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the solvent under reduced pressure
  10. customgave a brown oil which
  11. customwas purified by column chromatography (silica gel, hexane/AcOEt=19/1)

Sources & evidence

ORD record
ord-68b59cd27fee4b51aaa9fb68473acee1
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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