Water → HCID 86644604, compound

HRID 1966225Notes

Reaction equation

HRID 1966225 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:12][CH2:13][O:14][CH3:15].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:13][O:14][CH3:15])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 86644604HCID 86644604, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-hydroxypyridine (1 mmol) is dissolved in DMF (2.5 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min 1-Bromo-2-methoxy-ethane (1.1 eq.) is added and the reaction solution is stirred 3 days. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. 2-Bromo-5-(2-methoxyethoxy)-pyridine is obtained after column chromatography as colorless powder in a yield of 42%; HPLC (method C): 1.48 min; LC-MS (method A): 1.11 min, 231.95 (M+H+).

Workup

  1. extractionextracted with methyl-tert.-butyl ether
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1044a7776fed4ce7a995d006812eb10d
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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