Dimethyl Sulfoxide → 5-(4-Fluorophenoxy)furan-2-carbaldehyde

HRID 1927271Notes

Reaction equation

HRID 1927271 reaction equation
CS(C)=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[H-].[Na+].[N+]([C:18]1[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=1)([O-])=O>O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:18]2[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 97324-FluorophenolHCID 127745-NitrofurfuralHCID 24758Sodium hydride

Product 1

HCID 110419065-(4-Fluorophenoxy)furan-2-carbaldehydeYield 24.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of DMSO (50 mL) of p-fluorophenol (3.6 g) was added NaH (1.3 g/60% in oil) at room temperature, which was stirred for 15 minutes at room temperature. 5-Nitro-furan-2-carbaldehyde (5.0 g) was then added thereto, which was stirred for 40 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1) to obtain 5-(4-fluoro-phenoxy)-furan-2-carbaldehyde (1.6 g).

Workup

  1. stirringwhich was stirred for 40 minutes at room temperature
  2. extractionwas then extracted with ethyl acetate
  3. customThe solvent was evaporated from the organic layer under a reduced pressure
  4. customthe residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f791320e6571433aa9e1797e22850721
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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