Lithium Hydroxide → (2E)-2-(3-chloro-4-methylsulfonylphenyl)-2-(2-methylpropoxyimino)acetic acid
Reaktionsgleichung
C[O:2][C:3](=[O:22])/[C:4](/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([Cl:21])[CH:12]=1)=[N:5]/[O:6][CH2:7][CH:8]([CH3:10])[CH3:9].[OH-].[Li+]>CO>[Cl:21][C:13]1[CH:12]=[C:11](/[C:4](=[N:5]\[O:6][CH2:7][CH:8]([CH3:10])[CH3:9])/[C:3]([OH:22])=[O:2])[CH:16]=[CH:15][C:14]=1[S:17]([CH3:20])(=[O:19])=[O:18]Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
(E)-(3-Chloro-4-methanesulfonyl-phenyl)-isobutoxyimino-acetic acid methyl ester (326 mg, 0.94 mmol) was dissolved in methanol (9.4 mL) and cooled to 0° C. A 2.0 N aqueous solution of lithium hydroxide (1.41 mL, 2.82 mmol) was added dropwise and the cooling bath was removed. After stirring 25 min, the reaction mixture was diluted with chloroform (175 mL) and washed with 0.2 M aqueous potassium bisulfate solution (50 mL). The aqueous phase was extracted with chloroform (75 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford (E)-(3-chloro-4-methanesulfonyl-phenyl)-isobutoxyimino-acetic acid as a faintly yellow semi-solid (352 mg, >100%), which was used without further purification.
Aufarbeitung
- customthe cooling bath was removed
- additionthe reaction mixture was diluted with chloroform (175 mL)
- washwashed with 0.2 M aqueous potassium bisulfate solution (50 mL)
- extractionThe aqueous phase was extracted with chloroform (75 mL)
- dry with materialthe combined organic phases were dried over magnesium sulfate
- customevaporated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-f315a06cc23b4791831b8ea35a308b00
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07902248B2
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