Acetic Acid → Ethyl 5-(2-(4-nitrophenyl)-3-oxobutyl)-2-furancarboxylate

HRID 1602572Notes

Reaction equation

HRID 1602572 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.C(O)(=O)C>CN(C)C=O.C(OCC)C.O>[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

8

Reactant 4

HCID 176Acetic AcidHCID 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 105.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

3.00 g of 4-nitrophenylacetone in 50 ml of dimethylformamide was mixed with 0.70 g of 60% oily sodium hydride under cooling with ice under stirring and stirred at the same temperature for 10 minutes. After addition of 3.40 g of ethyl 5-(chloromethyl)-2-furancarboxylate in 5 ml of dimethylformamide, the reaction solution was stirred at room temperature for 2.5 hours. The reaction solution was acidified with acetic acid, and water and ethyl ether were added for extraction. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The desiccant was filtered off, and 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 give 5.84 g of the title compound as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred at the same temperature for 10 minutes
  3. stirringthe reaction solution was stirred at room temperature for 2.5 hours
  4. additionwere added for extraction
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→2/1]

Sources & evidence

ORD record
ord-f09896c6826b413e90983cd4fa9063fd
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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