Water → (5-Methylpyridin-3-yl)methanol

HRID 1186417Notes

Reaction equation

HRID 1186417 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:13]=[C:12]([C:14](OC)=[O:15])[CH:11]=[N:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[OH:15][CH2:14][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([CH3:7])[CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 256308Methyl 5-methylpyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11962777(5-Methylpyridin-3-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (552 mg, 14.5 mmol) was suspended in tetrahydrofuran (10 mL). To this, a tetrahydrofuran solution (10 mL) of methyl 5-methyl nicotinate (1.00 g, 14.5 mmol) was slowly added at 0° C. and the mixture was stirred at the same temperature for 30 minutes. The reaction was stopped by successive addition of water (0.552 mL), a 15% aqueous sodium hydroxide solution (0.552 mL) and water (1.66 mL) to the reaction mixture. The mixture was stirred at room temperature for 30 minutes and then filtered through Celite. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 3-hydroxymethyl-5-methylpyridine (972 mg, yield: 100%).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. filtrationfiltered through Celite
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-36e913dc54da45f387da44640a188474
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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