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

HRID 443284

Reaction equation

HRID 443284 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-a1abab0c1cf143da8767ee054720a160
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Linked notes

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