2-Bromoethanol → 2-[(5-Methylpyridin-2-yl)oxy]ethanol

HRID 1097259Notes

Reaction equation

HRID 1097259 reaction equation
Br[CH2:2][CH2:3][OH:4].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:2][CH2:3][OH:4])=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178426911HCID 178426911, compound

Product 1

HCID 207951692-[(5-Methylpyridin-2-yl)oxy]ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.291 ml (4.12 mmol) of 2-bromoethanol, of 0.3 g (2.75 mmol) of 2-hydroxy-5-methylpyridine and of 0.85 g (6.18 mmol) of potassium carbonate in 3 ml of dimethylformamide is vigorously stirred for 12 hours at reflux. The mixture is subsequently diluted with 100 ml of water and extracted with 100 ml of dichloromethane. The organic phase is washed with 50 ml of water, dried over sodium sulphate, concentrated under reduced pressure and then chromatographed on a silica column, elution being carried out with a mixture of hexane and ethyl acetate. The expected product is thus isolated.

Workup

  1. temperatureat reflux
  2. extractionextracted with 100 ml of dichloromethane
  3. washThe organic phase is washed with 50 ml of water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a silica column, elution
  7. additionbeing carried out with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-8965f48bb51349a691d45aacbc04b576
Source dataset
uspto-grants-2012_03
Patent number
US08143248B2

Reaction notes

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