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

HRID 1170653

Reaktionsgleichung

Reaktionsgleichung von HRID 1170653
[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-5f272bfbdb2243eb8c4502e1ff98021d
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825238B2

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