Potassium Carbonate → HCID 12052028, compound

HRID 1387696Notes

Reaction equation

HRID 1387696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CC(C)=O>[CH2:21]([O:20][C:18](=[O:19])[CH:17]([S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 12052028HCID 12052028, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-methoxybenzenethiol (2.5 gm, 14 mmol) and anhydrous K2CO3 (4.0 gm, excess) in dry acetone (100 ml), ethyl 2-bromo-propionate (3.0 gm, 16 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, reaction was allowed to cool, filtered and the reaction mixture was concentrated to a residue. The residue was extracted with chloroform and washed with H2O and the organic layer dried over MgSO4, filtered and concentrated to afford 2-(4methoxy-phenylsulfanyl)-propionic acid ethyl ester as a light yellow oil. Yield 3.6 gms (94%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 8 hours with good stirring
  3. customAt the end, reaction
  4. temperatureto cool
  5. filtrationfiltered
  6. concentrationthe reaction mixture was concentrated to a residue
  7. extractionThe residue was extracted with chloroform
  8. washwashed with H2O
  9. dry with materialthe organic layer dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5f6f321119d34855b3efc9a3d702cbdf
Source dataset
uspto-grants-2001_07
Patent number
US06268504B1

Reaction notes

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