Methanol → alpha-Methyl-4-pyridinemethanol

HRID 872437Notes

Reaction equation

HRID 872437 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO>O>[N:7]1[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 142824-Acetylpyridine

Product 1

HCID 90919alpha-Methyl-4-pyridinemethanolYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-acetylpyridine (2.50 g, 20.6 mmol) in methanol (25 ml) sodium borohydride (1.56 g, 41.2 mmol) was added in portions. After stirring overnight at RT water was added and the mixture was evaporated to dryness in vacuo. The product was taken into ethyl acetate. The solvent was evaporated to give 2.53 g of the title compound. 1H NMR (400 MHz, DMSO-d6): 1.32 (3H, d), 4.69-4.75 (1H, m), 5.38 (1H, d), 7.34 (2H, d), 8.49 (2H, d).

Workup

  1. additionwas added
  2. customthe mixture was evaporated to dryness in vacuo
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6519bba8ef7f42eb8e19d6bea0800be8
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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