Methanol → (3-Chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl ester

HRID 600942

Reaktionsgleichung

Reaktionsgleichung von HRID 600942
[CH3:1][O:2][C:3](=[O:15])[C:4]([C:6]1[CH:11]=[CH:10][C:9](SC)=[C:8]([Cl:14])[CH:7]=1)=[O:5].O[O:17][S:18]([O-:20])=O.[K+].[CH3:22]O>O>[CH3:1][O:2][C:3](=[O:15])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:18]([CH3:22])(=[O:20])=[O:17])=[C:8]([Cl:14])[CH:7]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 12069497(3-Chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid methyl esterHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 67482571(3-Chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl esterAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(3-Chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid methyl ester (prepared as in PCT WO 2004/052869 A1, Example 1, 1.89 g, 7.72 mmol) and oxone (14.26 g, 23.3 mmol) were combined in a mixture of water (4 mL) and methanol (40 mL) and stirred for 4 h. The methanol was evaporated in vacuo and the remaining mixture was treated with water (30 mL) and extracted with ethyl acetate (3×40 mL). The combined organic phases were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes) to afford (3-chloro-4-methanesulfonyl-phenyl)-oxo-acetic acid methyl ester (1.27 g, 60%) as a white solid: H1-NMR (400 MHz, CDCI3) δ=3.32 (3H, s), 4.03 (3H, s), 8.14 (1H, dd, J=8.0 Hz, J=1.6 Hz), 8.23 (1H, d, J=1.6 Hz), 8.30 (1H, d, J=8.0 Hz).

Aufarbeitung

  1. customThe methanol was evaporated in vacuo
  2. additionthe remaining mixture was treated with water (30 mL)
  3. extractionextracted with ethyl acetate (3×40 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3d1033ee86e849ee93e7aea969b0928f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902248B2

Verknüpfte Notizen

Wird geladen…