Diethyl Oxalate → Lithium 3-ethoxycarbonyl-2-methyl-3-oxo-1-(4-trifluoromethyl-phenyl)-propan-1-olate

HRID 526709

Reaktionsgleichung

Reaktionsgleichung von HRID 526709
C[Si]([N-][Si](C)(C)C)(C)C.[Li+:10].[F:11][C:12]([F:24])([F:23])[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:22])[CH2:20][CH3:21])=[CH:15][CH:14]=1.[C:25]([O:32][CH2:33][CH3:34])(=[O:31])[C:26]([O:28]CC)=O>CC1CCCCC1>[CH2:33]([O:32][C:25]([C:26](=[O:28])[CH:20]([CH3:21])[CH:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]([F:11])([F:23])[F:24])=[CH:18][CH:17]=1)[O-:22])=[O:31])[CH3:34].[Li+:10]

Komponenten

5

Edukt 3

HCID 7268Diethyl OxalateHCID 136554p-TrifluoromethylpropiophenoneHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 89907367Lithium 3-ethoxycarbonyl-2-methyl-3-oxo-1-(4-trifluoromethyl-phenyl)-propan-1-olate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7962MethylcyclohexaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 118 ml of lithium bis(trimethylsilyl)amide (Lithium Hexamethyldisilazide; 0.9 M in methylcyclohexane) was added dropwise over 15 min 20 g of 1-(4-Trifluoromethyl-phenyl)-propan-1-one in 51 ml methylcyclohexane at while maintaining the reaction mixture at 15-25° C. After stirring for 2 h, 15 ml of diethyl oxalate were added dropwise over 30 min and the reaction mixture was stirred for 16 h. Then, the precipitated product was collected by filtration and washed with n-heptane. The isolated crude product was used in the next reaction step after drying in vacuo. Yield: 19 g.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 16 h
  2. filtrationThen, the precipitated product was collected by filtration
  3. washwashed with n-heptane
  4. customThe isolated crude product
  5. customwas used in the next reaction step
  6. customafter drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-279f4601fcee4807b53a4ee69d049440
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346762B2

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