2-Chloro-6-methylpyridine-4-carboxylic acid → (2-Chloro-6-methylpyridin-4-yl)methanol

HRID 1068466Notes

Reaction equation

HRID 1068466 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[C:10]([CH3:17])[N:9]=1>C(OCC)C>[Cl:7][C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([CH3:17])[N:9]=1

Participants

4

Reactant 2

HCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a slurry of lithium aluminum hydride (0.45 g, 11.9 mmol) in anhydrous diethyl ether (40 mL) at 0° C., a solution of 2-chloro-6-methylpyridine-4-carboxylic acid (2.0 g, 11.7 mmol) in diethyl ether (30 mL) was added. The resulting mixture was stirred at room temp. overnight, and quenched with successive addition of water (0.45 mL), 15% aqueous NaOH (0.45 mL), and water (1.35 mL). The resultant slurry was stirred at room temp. for 30 min., and filtered through a small plug of Celite. The filtrate was washed brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide 2-chloro-4-hydroxymethyl-6-methylpyridine.

Workup

  1. customquenched with successive addition of water (0.45 mL), 15% aqueous NaOH (0.45 mL), and water (1.35 mL)
  2. stirringThe resultant slurry was stirred at room temp. for 30 min.
  3. filtrationfiltered through a small plug of Celite
  4. washThe filtrate was washed brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-47bea60781c048958e9b18df0643327c
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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