Potassium Carbonate → Ethyl 2-(4-methoxyphenyl)sulfanylacetate

HRID 991110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991110
ON[C:3]([C:5]1([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28]C3C=CC=CC=3)=[CH:23][CH:22]=2)(=O)=O)CCN(CC2C=CC=CC=2)CC1)=[O:4].C[O:36][C:37]1C=CC(S)=C[CH:38]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:37]([O:36][C:3](=[O:4])[CH2:5][S:18][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[CH3:38]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 99130531-benzyl-4-(4-(benzyloxy)phenylsulfonyl)-N-hydroxypiperidine-4-carboxamide

Produkt 1

HCID 1482371Ethyl 2-(4-methoxyphenyl)sulfanylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

1-Benzyl-4-(4-benzyloxy-benzenesulfonyl)-piperidine-4-carboxylic acid hydroxyamide To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 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, the reaction mixture 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 0.5N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy- phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield: 4.4 g (100%); MS; 227 (M+H)+

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-73ed2f0af7604acdb92d922a13ade86d
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462073B2

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