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

HRID 1901081Notes

Reaction equation

HRID 1901081 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].COC([C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][NH:12]1)=O.O.[OH-].[Na+].C[CH2:22][O:23]CC>>[OH:23][CH2:22][C:16]1[C:11]([CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 5

HCID 962Water2×HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 121457151HCID 121457151, compound

Product 1

HCID 302564(2-Methylpyridin-3-yl)methanol

Procedure

To a suspension of lithium aluminum hydride (2.0 g, 53 mmol) in anhydrous ether (300 ml) was added a solution of methyl-2-methylpyridine carboxylate (8.14 g, 53.8 mmol) in 100 ml anhydrous ether over 20 min. The reaction mixture was stirred 1.5 h at room temp. and the treated carefully in succession with 2 ml of water, 2 ml of 15% aqueous sodium hydroxide, and 6 ml of water. The white slurry was stirred 1 h at room temp. and then filtered through Celite. After several washings with ether, the combined filtrates were washed with brine, dried (MgSO4), and concentrated in vacuo to a pale yellow oil. This material was purified by column chromatography on silica with 5% methanol/chloroform as eluent to afford the product as a colorless oil.

Workup

  1. stirringThe white slurry was stirred 1 h at room temp.
  2. filtrationfiltered through Celite
  3. washAfter several washings with ether
  4. washthe combined filtrates were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to a pale yellow oil
  7. customThis material was purified by column chromatography on silica with 5% methanol/chloroform as eluent

Sources & evidence

ORD record
ord-6f8684c68f914f21979e5c543d4a1e9c
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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