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Cesium carbonate → Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetate

HRID 68320
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 68320
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:19][N:20]=[C:21]([C:23]1[O:27][C:26]([N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:25][CH:24]=1)[CH3:22]>CN(C=O)C>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:19][N:20]=[C:21]([C:23]2[O:27][C:26]([N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:25][CH:24]=2)[CH3:22])=[CH:4][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86699627Diethyl 2,2'-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate

Produkt 1

HCID 86699628Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 1-(bromomethyl)-4-(trifluoromethyl)benzene (200 mg, 0.84 mmoles) in DMF (2 mL), cesium carbonate (408 mg, 1.26 mmoles) was added followed by addition of diethyl 2,2′-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate (262 mg, 0.84 mmoles) at 25° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 18 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography (Eluent: 15% ethyl acetate in hexane) to yield 295 mg (75%) product as thick liquid.

Aufarbeitung

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography (Eluent: 15% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-af5626932dec4aa0816055572b30561f
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822414B2

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