Dimethylformamide → 5-Phenyl-2-furaldehyde

HRID 1195914

Reaction equation

HRID 1195914 reaction equation
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[C:11]1([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>>[C:11]1([C:17]2[O:18][C:19]([CH:3]=[O:4])=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 5193632-Phenylfuran

Product 1

HCID 27694205-Phenyl-2-furaldehydeYield 83.7%

Conditions

Temperature
80 °C

Procedure

To a 0° C. solution of N,N-dimethylformamide (1.9 mL, 24.97 mmol) in a three-neck flask equipped with a condenser was added POCl3 (0.65 mL, 6.94 mmol) dropwise via syringe with stirring. When the heat of the reaction subsided, 2-phenylfuran (1.0 g, 6.94 mmol) was added. The reaction was warmed to 80° C. and stirred overnight. The solution was cooled to room temperature and then neutralized to pH 8 with aqueous saturated sodium acetate. The mixture was extracted with ether (3×30 mL), dried over MgSO4, filtered and evaporated. Chromatography (silica gel, 20% ether/hexanes) yielded 1.0 g (83%) of 5-phenyl-2-furaldehyde.

Workup

  1. temperatureWhen the heat of the reaction
  2. stirringstirred overnight
  3. temperatureThe solution was cooled to room temperature
  4. extractionThe mixture was extracted with ether (3×30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e08d53aab55a4eb091b1ace0f0af8fd9
Source dataset
uspto-grants-1992_05
Patent number
US05112848

Linked notes

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