Sodium Carbonate → HCID 68815907, Verbindung

HRID 735039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735039
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](OB(O)O)=[CH:24][CH:23]=1>O1CCOCC1.CO>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:24][CH:23]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 688115Ethyl trans-4-BromocinnamateHCID 17810664p-Chlorophenylboric acid

Produkt 1

HCID 68815907HCID 68815907, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

173 mg (0.15 mmol) of tetrakistriphenylphosphine palladium and 4.4 mL (8.8 mmol) of a 2M sodium carbonate solution is added at ambient temperature to a solution of 1.124 g (4.04 mmol) of ethyl (E)-3-(4-bromophenyl)acrylate in 50 mL of dioxane. 0.689 g (4.404 mmol) of 4-chlorophenylboric acid dissolved in 10 mL of methanol is added to this reaction mixture and refluxed for 5 hours. The reaction mixture is evaporated down, the residue is taken up in dichloromethane, and extracted with water. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether/ethyl acetate (9:1)). Yield: 0.94 g (74.4% of theory); C17H15ClO2 (M=286.76); calc.: molecular ion peak (M+H)+: 287/289; found: molecular ion peak (M+H)+: 287/289; Rf value: 0.44 (silica gel, petroleum ether/ethyl acetate (40:10)).

Aufarbeitung

  1. additionis added to this reaction mixture
  2. temperaturerefluxed for 5 hours
  3. customThe reaction mixture is evaporated down
  4. extractionextracted with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-703776c8abdd43cfa88005a55fef66f0
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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