Potassium Carbonate → Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

HRID 490762Notes

Reaction equation

HRID 490762 reaction equation
Cl[CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([SH:19])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][C:3](=[O:10])[CH2:2][S:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH3:11])[CH:14]=1)[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69484Ethyl 4-chloroacetoacetateHCID 849893-Methoxybenzenethiol

Product 1

HCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-chloroacetoacetate (32.6 g, 0.188 mol), 3-methoxythiophenol (25.1 g, 0.179 mol) and DMF (700 mL) are combined and degassed by bubbling nitrogen through the stirred mixture for about 10 min, then potassium carbonate (50 g, 0.36 mol) is added to the stirred mixture in one batch. This mixture is stirred under nitrogen at room temperature for 2 h, the mixture is filtered to remove potassium carbonate, then diluted with ethyl acetate. The resulting solution is washed with water, then 5% aq. NaCl. The combined organics are washed with brine, dried over Na2SO4. Concentration yields the title compound as yellow liquid. This material is used without purification.

Workup

  1. customdegassed
  2. customby bubbling nitrogen through the stirred mixture for about 10 min
  3. filtrationthe mixture is filtered
  4. customto remove potassium carbonate
  5. additiondiluted with ethyl acetate
  6. washThe resulting solution is washed with water
  7. washThe combined organics are washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationConcentration

Sources & evidence

ORD record
ord-5726944cfddf4f12b0d0867bc45a60eb
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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