Epibromohydrin → HCID 20309567, Verbindung

HRID 596693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596693
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([OH:19])=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])(=[O:3])[CH3:2].[CH2:20]([CH:22]1[O:24][CH2:23]1)Br>C(C(C)=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:19][CH2:20][CH:22]2[O:24][CH2:23]2)=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 18430EpibromohydrinHCID 20309539HCID 20309539, Verbindung

Produkt 1

HCID 20309567HCID 20309567, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

Methyl 3-(5-acetamido-2-hydroxybenzoyl)propionate (0.75g) anhydrous potassium carbonate (0.39g), epibromohydrin (0.78g) and dry methyl ethyl ketone (20 ml) were stirred and heated under reflux for 16 hours. The cooled reaction mixture was filtered, the filtrate evaporated under reduced pressure and the residual oil purified by elution from a silica column with chloroform/methanol. Methyl 3-[5-acetamido-2-(2,3-epoxypropoxy)benzoyl]propionate was obtained as an oil which solidified, (0.52g, 57%, m.p. 84°-87° C; M+, 321, M 321).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate evaporated under reduced pressure
  6. customthe residual oil purified by elution from a silica column with chloroform/methanol

Quellen und Nachweise

ORD-Eintrag
ord-e85a9f23b1cc4588bbf96612d8ac5f97
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011321

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