Dimethylformamide → 4,5-Dimethyl-2-furaldehyde

HRID 651479Notes

Reaction equation

HRID 651479 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[O:8][CH:9]=[CH:10][C:11]=1[CH3:12].[OH-].[Na+].CN([CH:18]=[O:19])C>O>[CH3:12][C:11]1[CH:10]=[C:9]([CH:18]=[O:19])[O:8][C:7]=1[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 343372,3-Dimethylfuran

Product 1

HCID 6434064,5-Dimethyl-2-furaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to the procedure of S. F. Martin, et al. J. Org. Chem. 1984, 49, 2512-2516, phosphorus oxychloride (10.7 mL, 114.4 mmol) was added dropwise to a stirred, ambient temperature solution of 2,3-dimethylfuran (10 g, 104 mmol) in DMF (150 mL) under a dry nitrogen atmosphere over a period of 30 min. After 3 h., the reaction mixture was hydrolized with 2.5 N aq. sodium hydroxide and further diluted with water (50 mL). Aqueous mixture was extracted with dichloromethane (2×300 mL). The combined dichloromethane extracts were washed with water, dried with brine and purified by silica gel flash chromatography (eluent: ethyl acetate) to provide a yellow oil (9.8 g, 76%); MS (ESI): [M+H]+, 125.1.

Workup

  1. extractionAqueous mixture was extracted with dichloromethane (2×300 mL)
  2. washThe combined dichloromethane extracts were washed with water
  3. dry with materialdried with brine
  4. custompurified by silica gel flash chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-51fe923c52e84865bdcae201dd074780
Source dataset
uspto-grants-2001_08
Patent number
US06281238B1

Reaction notes

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