2-Bromoethanol → HCID 54199935, compound

HRID 1790803Notes

Reaction equation

HRID 1790803 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 54199935HCID 54199935, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ecce1927c95d42dab8d8a8a497f449ad
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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