1-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene → 1-Chloro-2-(4-ethyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

HRID 1041939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041939
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][CH3:28])=[CH:25][CH:26]=1

Komponenten

5

Edukt 1

HCID 866006811-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Produkt 1

HCID 866162451-Chloro-2-(4-ethyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.87 g 1-chloro-2-(4-ethynyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene are dissolved in 10 ml of ethyl acetate and 5 ml of ethanol. 0.3 g 10% palladium on carbon are added and the resultant mixture is stirred under hydrogen atmosphere (1 atm) overnight. The reaction mixture is filtered over Celite and the filtrate is concentrated. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered over Celite
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

Quellen und Nachweise

ORD-Eintrag
ord-f472de2b5a894357a52f21ad0044be65
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557782B2

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