Water → (6-Methoxypyridin-3-yl)methanol

HRID 1042625Notes

Reaction equation

HRID 1042625 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.C(OCC)C>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([CH2:7][OH:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 586039Methyl 6-methoxypyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12259941(6-Methoxypyridin-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-methoxynicotinate (1.00 g, 5.98 mmol) in 20 mL of THF at 0° C. under an atmosphere of nitrogen was added lithium aluminum hydride (1.0 M in THF, 9.0 mL, 9.0 mmol) dropwise. After 30 min, the reaction was warmed to rt, and after 30 min, the reaction was recooled to 0° C., diluted with diethyl ether, and treated with water (0.34 mL), 15% aqueous sodium hydroxide (0.34 mL), and additional water (1.02 mL). The mixture was dried over magnesium sulfate and warmed to rt. After 15 min, the mixture was filtered through celite and concentrated in vacuo to provide (6-methoxypyridin-3-yl)methanol that gave a proton NMR spectra consistent with theory.

Workup

  1. waitafter 30 min
  2. customwas recooled to 0° C.
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. temperaturewarmed to rt
  5. waitAfter 15 min
  6. filtrationthe mixture was filtered through celite and
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4592b60e730f488c8ffd49d90c7d5527
Source dataset
uspto-grants-2013_10
Patent number
US08557992B2

Reaction notes

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