Water → ethyl 5-(4-chlorophenyl)-2-methyl-3-furoate

HRID 1876956Notes

Reaction equation

HRID 1876956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([CH3:13])=[C:10]([C:14]([O:16][CH2:23][CH3:24])=[O:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27421815-(4-chlorophenyl)-2-methylfuran-3-carboxylic acid

Product 1

HCID 2742179ethyl 5-(4-chlorophenyl)-2-methyl-3-furoateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(4-chlorophenyl)-2-methyl-3-furancarboxylic acid (4.7 g), potassium carbonate (2.8 g) and ethyl iodide (3.7 g) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 4 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (5.0 g, 95%) as a yellow crystal.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9ee9b7a08b6e4909b97d5fdb8db4bc48
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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