Ethyl chloroacetate → Ethyl-5-[(hydroxyimino)methyl]-2-nitro-3-thiopheneacetate

HRID 1860269

Reaktionsgleichung

Reaktionsgleichung von HRID 1860269
CC(C)([O-])C.[K+].[N+:7]([C:10]1[S:14][C:13]([CH:15]=[N:16][OH:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].Cl[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:11]1[CH:12]=[C:13]([CH:15]=[N:16][OH:17])[S:14][C:10]=1[N+:7]([O-:9])=[O:8])[CH3:24]

Komponenten

5

Edukt 3

HCID 7751Ethyl chloroacetateHCID 3505165-Nitro-2-thiophenecarboxaldehyde oximeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 85801896Ethyl-5-[(hydroxyimino)methyl]-2-nitro-3-thiopheneacetateAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

Potassium tertiary-butoxide (960 mg, 8.6 mmol) was dissolved in N,N-dimethylformamide (10 ml) and the solution cooled to −30° C. A solution of 5-nitro-2-thiophenecarboxaldehyde oxime (400 mg, 2.86 mmol) and ethyl chloroacetate (356 mg, 2.86 mmol) was added dropwise in dry N,N-dimethylformamide (5 ml) over 5 minutes. The reaction mixture was stirred at −30° C. for 30 minutes then quenched with 2M HCl (50 ml), diluted with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel using hexane/diethyl ether (1:2) as eluent to give 200 mg of ethyl-5-[(hydroxyimino)methyl]-2-nitro-3-thiopheneacetate as a tan solid. MS(ES): m/e 227 [M+H].

Aufarbeitung

  1. customthen quenched with 2M HCl (50 ml)
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3725d1bfa4d54d478308ee4da6cc06a7
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528653B2

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