Hydrogen Bromide → 2-Bromomethyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranos-1-yl)-benzonitrile
Reaktionsgleichung
[BrH:1].C1(O[CH2:9][C:10]2[CH:17]=[C:16]([C@:18]3([O:36][C@H:35]([CH2:37][O:38][C:39](=[O:41])[CH3:40])[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:20]3[O:21][C:22](=[O:24])[CH3:23])[OH:19])[CH:15]=[CH:14][C:11]=2[C:12]#[N:13])C=CC=CC=1.C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:1][CH2:9][C:10]1[CH:17]=[C:16]([C@:18]2([O:36][C@H:35]([CH2:37][O:38][C:39](=[O:41])[CH3:40])[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:20]2[O:21][C:22](=[O:24])[CH3:23])[OH:19])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]Komponenten
6
Reaktionsbedingungen
- Temperatur
- 55 °C
Versuchsvorschrift
A 33% solution of hydrobromic acid in acetic acid (15 mL) is added to a solution of 2-phenyloxymethyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzonitrile (0.71 g) and acetic anhydride (0.12 mL) in acetic acid (10 ml). The resulting solution is stirred at 55° C. for 6 h and then cooled in an ice-bath. The reaction mixture is neutralized with chilled aqueous potassium carbonate solution, and the resultant mixture is extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is taken up in ethyl acetate/cyclohexane (1:5), and the precipitate is separated by filtration and dried at 50° C. to give the product.
Aufarbeitung
- temperaturecooled in an ice-bath
- extractionthe resultant mixture is extracted with ethyl acetate
- dry with materialThe combined organic extracts are dried over sodium sulfate
- customthe solvent is removed under reduced pressure
- customthe precipitate is separated by filtration
- customdried at 50° C.
- customto give the product
Quellen und Nachweise
- ORD-Eintrag
- ord-711d0b8ddfc043759b4ba034ed970f34
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08551957B2
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