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

HRID 989995

Reaktionsgleichung

Reaktionsgleichung von HRID 989995
[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. Yield: 8 g=71%

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-bf93b888e5ab4bcd9be5e6dda82bab73
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458772B1

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