Water → (2-Methoxypyridin-3-yl)methanol

HRID 856703Notes

Reaction equation

HRID 856703 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[N:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12].O.[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[C:10]([CH2:11][OH:12])=[CH:15][CH:16]=[CH:17][N:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10820973Methyl 2-methoxypyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10630565(2-Methoxypyridin-3-yl)methanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aluminum lithium hydride (1.43 g) in THF (126 ml) was added a solution of methyl 2-methoxynicotinate (6.3 g) in THF (63 ml) at 0° C. The mixture was stirred at room temperature for 2 hours, and water (6.3 ml), 15% aqueous solution of sodium hydroxide (6.3 ml) and water (18.9 ml) were sequentially added to the solution at 0° C. The mixture was filtered with Celite, and washed with methanol. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give (2-methoxy-3-pyridinyl)methanol (5.0 g).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. washwashed with methanol
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a32d1454d194535ae3c67301098c3d4
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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