Potassium Carbonate → 2-Methoxy-5-(methoxymethoxy)pyridine

HRID 1471680Notes

Reaction equation

HRID 1471680 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH3:16][O:17][CH2:18]Br>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:16][O:17][CH3:18])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 83093Bromomethyl methyl etherHCID 116223355-Hydroxy-2-methoxypyridine

Product 1

HCID 120277842-Methoxy-5-(methoxymethoxy)pyridineYield 49,257.801%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-methoxypyridin-3-ol (25 g, 0.2 mol) and K2CO3 (82.8 g, 0.6 mol) in DMF (250 mL) was added bromomethyl methyl ether (30 g, 0.24 mmol) slowly at rt for a period of 1 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified on silica gel with 25% EtOAc/hexanes as eluent to give 2-methoxy-5-(methoxymethoxy)pyridine (20 g, 59%) as a colorless oil. LRMS (M+H+) m/z 170.1

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on silica gel with 25% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-933c4e871b9b4fc18f90e8b5eb4b68b1
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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