Potassium Carbonate → HCID 12052028, compound

HRID 991022Notes

Reaction equation

HRID 991022 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

Procedure

To stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), ethyl 2-bromo-propionate (3.6 gm, 20 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 and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O and 0.5 N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated to afford 2-(4-methoxy-phenylsulfanyl)-propionic acid ethyl ester as a light yellow oil. Yield 4.5 gms (94%); MS; 241 (M+H)+.

Workup

  1. additionwas added in a round bottom flask
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 8 hours with good stirring
  4. customAt the end, reaction
  5. temperatureto cool
  6. filtrationthe potassium salts were filtered off
  7. concentrationthe reaction mixture was concentrated
  8. extractionThe residue was extracted with chloroform
  9. washwashed with H2O and 0.5 N NaOH solution
  10. washThe organic layer was further washed well with water
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-fe2f7096edf94216b0fbc56dfab7b4d4
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

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