Methyl 4-Chloropicolinate → (4-Chloropyridin-2-yl)methanol

HRID 1068468Notes

Reaction equation

HRID 1068468 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14](OC)=[O:15])[CH:9]=1>C(OCC)C>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][OH:15])[CH:9]=1

Participants

4

Reactant 2

HCID 820890Methyl 4-ChloropicolinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2763167(4-Chloropyridin-2-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 methyl 4-chloro-pyridine-2-carboxylate (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 with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide 4-chloro-2-hydroxymethylpyridine.

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 with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7b523d44b6f34da0b086dc611073e20f
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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