Water → 5-(4-Chloro-phenoxy)-furan-2-carbaldehyde

HRID 2080082Notes

Reaction equation

HRID 2080082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[N+]([C:14]1[O:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=1)([O-])=O.O>CS(C)=O.C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:14]2[O:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 127745-NitrofurfuralHCID 24758Sodium hydride

Product 1

HCID 112761115-(4-Chloro-phenoxy)-furan-2-carbaldehydeYield 53.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-chlorophenol (4.4 g, 33.6 mmol) in dimethylsulfoxide (30 mL) was added sodium hydride (1.34 g, 33.6 mmol, 60% in oil), and the solution was stirred at room temperature for 10 minutes. 5-Nitrofuran-2-carbaldehyde (4.0 g, 28 mmol) was added to this reaction solution, and the solution was stirred at room temperature for 5 minutes. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed with water 6 times. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane, then hexane:ethyl acetate=10:1, then 4:1), and the title compound (3.3 g, 14.9 mmol, 53.0%) was obtained as a yellow oil.

Workup

  1. stirringthe solution was stirred at room temperature for 5 minutes
  2. customwas then partitioned
  3. washthe organic layer was washed with water 6 times
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-58ab0424cb384006ab5f1c569bc7fde0
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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