Chloromethyl Methyl Ether → 1-[5-(Methoxymethoxy)-2-pyridinyl]ethanone

HRID 1807701Notes

Reaction equation

HRID 1807701 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:12])[CH3:11])=[N:8][CH:9]=1.[CH2:13](Cl)[O:14][CH3:15]>CN(C=O)C>[CH3:13][O:14][CH2:15][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:12])[CH3:11])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 124162311-(5-Hydroxypyridin-2-yl)ethan-1-one

Product 1

HCID 580927481-[5-(Methoxymethoxy)-2-pyridinyl]ethanoneYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH was added to a solution of 1 g (7.29 mmol) 1-(5-hydroxy-pyridin-2-yl)-ethanone (Anichem) in 15 ml DMF at 0° C. After stirring this mixture for 1 h, 0.78 ml (8.75 mmol) MOMCl was added at 0° C. Then the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was poured on water and extracted 2 times with EtOAc. The combinded organic layers were washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel (EtOAc, heptane) to yield 1.12 g of the pure title compound as an oil. LCMS (method L): tR=0.66 min, M+H=182.

Workup

  1. stirringThen the reaction mixture was stirred at room temperature for 2 h
  2. additionThe reaction mixture was poured on water
  3. extractionextracted 2 times with EtOAc
  4. washThe combinded organic layers were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silicagel (EtOAc, heptane)

Sources & evidence

ORD record
ord-ee564fe231c84e1abd64f6fd4bf3671d
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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