Water → HCID 23130351, compound

HRID 2080093Notes

Reaction equation

HRID 2080093 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].[N+]([C:15]1[O:19][C:18]([CH:20]=[O:21])=[CH:17][CH:16]=1)([O-])=O.O>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][C:15]1[O:19][C:18]([CH:20]=[O:21])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 1230512,4-Difluorophenol

Product 1

HCID 23130351HCID 23130351, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,4-difluorophenol (6.54 mL, 68.0 mmol) in dimethylsulfoxide (70 mL) was sodium hydride (4534 mg, 68.0 mmol, 60% in oil), which was then stirred for 40 minutes. 5-Nitro-2-furaldehyde (8000 mg, 56.7 mmol) was added to the reaction solution, and the solution was stirred at room temperature for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate), and the title compound (4134 mg, 18.44 mmol, 33%) was obtained.

Workup

  1. stirringthe solution was stirred at room temperature for 2 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-204258823487476a9145e5174985e4eb
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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