2-Bromoethanol → HCID 54199935, Verbindung

HRID 989985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989985
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[NH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][OH:29]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH2:27][CH2:28][OH:29])[CH:12]=2)=[O:10])=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 47143064HCID 47143064, Verbindung

Produkt 1

HCID 54199935HCID 54199935, VerbindungAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester (4.41 g, 17 mmol) and K2CO3 (2.58 g, 18.7 mmol) in DMF (100 mL) at room temperature, was added 2-bromoethanol (2.02 g, 16.2 mmol). The reaction mixture was stirred at 80° C. for 30 h, whereupon the DMF was evaporated under vacuum. The crude product was column chromatographed (silica gel, 2→5% MeOH in CH2Cl2), to give 3.91 g of 1-(2-hydroxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester.

Aufarbeitung

  1. customwas evaporated under vacuum
  2. customchromatographed (silica gel, 2→5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-485113f62ef24501a4d96706145b706e
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458772B1

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