Potassium Iodide → Ethyl 5-(2-(4-nitrophenyl)-3-oxobutyl)-2-furancarboxylate

HRID 850657

Reaction equation

HRID 850657 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:17][C:18]1[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:19]=1.[I-].[K+]>CN(C)C=O.C(OCC)C.O.C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:11](=[O:13])[CH3:12])[CH2:17][C:18]2[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:19]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 2193671-(4-Nitrophenyl)propan-2-oneHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 15458175Ethyl 5-(2-(4-nitrophenyl)-3-oxobutyl)-2-furancarboxylateYield 98.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

3.00 g of p-nitrophenylacetone was dissolved in 50 ml of dimethylformamide, and 0.70 g of 60% oily sodium hydride was added under cooling with ice with stirring, followed by stirring at the same temperature for 10 minutes. 5 ml of a dimethylformamide solution containing 3.40 g of ethyl 5-chloromethyl-2-furancarboxylate, and 3.05 g of potassium iodide were added thereto, followed by stirring at room temperature for 2.5 hours. Then, the reaction solution was acidified by an addition of acetic acid. Water and ethyl ether were added, and the mixture was extracted. Then, the organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→2/1) to obtain 5.48 g of the above-identified compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring at the same temperature for 10 minutes
  3. additionwere added
  4. stirringby stirring at room temperature for 2.5 hours
  5. extractionthe mixture was extracted
  6. washThen, the organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→2/1)

Sources & evidence

ORD record
ord-cab4db1d64754035bf70ebd8bb1d7916
Source dataset
uspto-grants-2000_01
Patent number
US06017956

Linked notes

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