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Triethyl phosphonoacetate → HCID 54164066, Verbindung

HRID 2397055
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2397055
CC(C)([O-])C.[K+].C(OP([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(OCC)=O)C.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:26]([CH:29]=1)[CH:27]=O.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:26]([CH:29]=1)[CH:27]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 13345Triethyl phosphonoacetateHCID 516892Sodium BicarbonateHCID 189868805-Chloro-2-(2-phenylethoxy)benzaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 54164066HCID 54164066, VerbindungAusbeute 168,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

In an argon gas stream, 3.49 g of potassium t-butoxide was added to a solution of 8.36 g of ethyl diethylphosphonoacetate in 100 ml of tetrahydrofuran under ice-cooling. The obtained mixture was then stirred at the same temperature for 1 hour. Next, a solution of 5.40 g of 5-chloro-2-(2-phenylethoxy)benzaldehyde in 30 ml of tetrahydrofuran was added dropwise to the reaction mixture and the resulting mixture was stirred at the same temperature for 1 hour and then at room temperature for 19 hours. After adding 30 ml of a saturated aqueous solution of sodium hydrogencarbonate, the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 11.56 g of crude ethyl 5-chloro-2-(2-phenylethoxy)cinnamate was obtained. Thus compound was not purified any more but used in the subsequent reaction as such.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  3. waitat room temperature for 19 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-828f0629d46641b48a09095f1074ce7e
Quelldatensatz
uspto-grants-1996_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05495046

Notizen zur Reaktion

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