Water → (6-Methylpyridin-3-yl)methanol

HRID 1830748Notes

Reaction equation

HRID 1830748 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1378606-Methylnicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of 6-methyl nicotinic acid (5.0 mmol) in tetrahydrofuran (10 mL) was added lithium aluminum hydride (20 mmol; 20 mL of a 1M solution in tetrahydrofuran.) dropwise. The reaction was stirred for 4 hours, treated sequentially with 1 mL of H2O, 1 mL of 15% aqueous sodium hydroxide, and 3 mL of H2O. The reaction was filtered and washed with tetrahydrofuran (3×50 mL). The filtrate was concentrated under reduced pressure to yield the alcohol as a clear viscous oil.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with tetrahydrofuran (3×50 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b0add999b164c18b936c16c2257e0c9
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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