Diethyl Oxalate → Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate

HRID 1510429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510429
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CCCC1.[CH3:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:19].[C:27]([O:34][CH2:35][CH3:36])(=[O:33])[C:28]([O:30]CC)=O>C(OCC)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C:18](=[O:19])[CH:17]([CH3:16])[C:28](=[O:30])[C:27]([O:34][CH2:35][CH3:36])=[O:33])=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 7268Diethyl OxalateHCID 8028TetrahydrofuranHCID 226974'-ChloropropiophenoneHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 5051380Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoateAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (30 mL, 30 mmol) in anhydrous diethyl ether (120 mL) under argon was cooled to −78° C. in a dry ice/acetone bath. A solution of 4-chloropropiophenone (5.0 g, 29.7 mmol) in anhydrous ether (24 mL) was added dropwise and the mixture was stirred an additional 45 minutes at −78° C. Diethyl oxalate (4.6 mL, 33.9 mmol) was added in one portion; the reaction was warmed to room temperature, and stirred overnight. The light yellow precipitate that formed was collected, washed with ether and dried under vacuum to obtain the lithium enolate of ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate (2.75 g, 10.0 mmol).

Aufarbeitung

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. customThe light yellow precipitate that formed
  4. customwas collected
  5. washwashed with ether
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3b5cd30040154919a6e1f47720c82fe2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211927B2

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