Methanol → 6-(Methoxymethyl)pyridin-3-ol

HRID 2074294Notes

Reaction equation

HRID 2074294 reaction equation
[CH3:1][O-:2].[Na+].CO.C1(S([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22]Br)=[N:20][CH:21]=2)(=O)=O)C=CC=CC=1>O>[CH3:1][O:2][CH2:22][C:19]1[N:20]=[CH:21][C:16]([OH:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10639974HCID 10639974, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 231457756-(Methoxymethyl)pyridin-3-olYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium methoxide (393 mg) was added to a methanol (20 ml) solution containing 5-(benzenesulfonyloxy)-2-(bromomethyl)pyridine (Beilstein Registry No. 7430370, 800 mg), followed by stirring at room temperature for 4 hours. Water was added to the reaction solution, followed by extraction with EtOAc. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: EtOAc) to obtain 6-(methoxymethyl)pyridin-3-ol (200 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: EtOAc)

Sources & evidence

ORD record
ord-db530bc2fe794e2cb51bc4d687f880ea
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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