Glyceraldehyde → Benzyl 4,5-dihydroxy-2-pentenoate

HRID 489063

Reaktionsgleichung

Reaktionsgleichung von HRID 489063
[CH2:1]([OH:6])[CH:2]([OH:5])[CH:3]=O.[Br-].[CH2:8]([O:15][C:16]([CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1C(CC)C1>[OH:5][CH:2]([CH2:1][OH:6])[CH:3]=[CH:18][C:16]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17]

Komponenten

4

Edukt 2

HCID 751GlyceraldehydeHCID 11214019(Benzyloxycarbonylmethyl)triphenylphosphonium bromide

Produkt 1

HCID 54529065Benzyl 4,5-dihydroxy-2-pentenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 78341,2-EpoxybutaneLösungsmittel

Versuchsvorschrift

A mixture of DL-glycerinaldehyde (4.5 g, 50 mmole) and (benzyloxycarbonylmethyl)-triphenyl-phosphoniumbromide (24.57 g, 50 mmole) in 100 ml 1,2-epoxybutane was refluxed overnight. The mixture was evaporated under vacuum and the product was isolated by silica gel column chromatography.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated under vacuum
  3. customthe product was isolated by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-274a806608864003b6ffad9050318002
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974802B2

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