Water → HCID 87416741, Verbindung

HRID 600945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600945
C[O:2][C:3](=[O:23])/[C:4](/[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([Cl:22])[CH:13]=1)=[N:5]/[O:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Li+].O>CO.C(Cl)(Cl)Cl>[Cl:22][C:14]1[CH:13]=[C:12](/[C:4](=[N:5]\[O:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)/[C:3]([OH:23])=[O:2])[CH:17]=[CH:16][C:15]=1[S:18]([CH3:21])(=[O:20])=[O:19]

Komponenten

6

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 87416800methyl (2E)-2-(3-chloro-4-methylsulfonylphenyl)-2-cyclopentyloxyiminoacetate

Produkt 1

HCID 87416741HCID 87416741, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(E)-(3-Chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid methyl ester (144 mg, 0.40 mmol) was dissolved in methanol (4 mL) and cooled in an ice bath. A 2.0 N solution of lithium hydroxide in water (0.60 mL, 1.2 mmol) was added dropwise. After stirring 1 h, the reaction mixture was diluted with chloroform (50 mL) and washed with 0.1 M aqueous potassium bisulfate (25 mL). The aqueous phase was extracted with chloroform (30 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford (E)-(3-chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid which was used in the next step without further purification: H1-NMR (400 MHz, CDCl3) δ=1.65 (4H, m), 1.88 (4H, m), 3.31 (3H, s), 4.97 (1H, m), 7.58 (1H, dd, J=8.2 Hz, J=1.1 Hz), 7.67 (1H, d, J=1.1 Hz), 8.19 (1H, d, J=8.2 Hz).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. washwashed with 0.1 M aqueous potassium bisulfate (25 mL)
  3. extractionThe aqueous phase was extracted with chloroform (30 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-93ac6b35d6474007821a7cc503a93a59
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902248B2

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