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

HRID 2070948Notes

Reaction equation

HRID 2070948 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O.CCOC(C)=O>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:8][CH:9]=[CH:10][N:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 7015327Methyl 2-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 302564(2-Methylpyridin-3-yl)methanolYield 72.7%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 1.5 g of methyl 2-methylnicotinate in 20 mL of THF at 0° C. was added 844 mg of LiAlH4. After 20 min., 0.84 mL of H2O, 0.84 mL of 15% aqueous NaOH, and 2.5 mL of brine. EtOAc was added, the ice bath removed, and stirring was continued for 1 h. The mixture was filtered through Celite and concentrated to give 889 mg of crude (2-methylpyridin-3-yl)methanol which was used without further purification.

Workup

  1. customthe ice bath removed
  2. waitwas continued for 1 h
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9b317ce76614640a047ca6192577c57
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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