Potassium Iodide → HCID 86611027, Verbindung

HRID 2245916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245916
[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]([OH:27])=[CH:23][CH:22]=1.Br[C:29]1([C:34]([O:36][CH3:37])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CO.O>[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]([O:27][C:29]2([C:34]([O:36][CH3:37])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:25][CH:26]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12531340Methyl 1-bromocyclopentane-1-carboxylateHCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Produkt 1

HCID 86611027HCID 86611027, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-chloro-4-(β-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene (0.46 g), 1-bromo-1-methoxycarbonylcyclopentane (0.87 g), potassium iodide (0.1 g) and potassium carbonate (0.5 g) in methanol (5 mL) is stirred at reflux for 16 h. After cooling to ambient temperature, water is added and the resultant mixture is extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. extractionthe resultant mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried (Na2SO4)
  4. customthe solvent is removed
  5. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c52f7a6318514153be78e70536a7a57f
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683160B2

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