4-Acetylpyridine → alpha-Methyl-4-pyridinemethanol

HRID 2176973Notes

Reaction equation

HRID 2176973 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4]>C(O)C>[N:9]1[CH:10]=[CH:11][C:6]([CH:3]([OH:5])[CH3:4])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 142824-AcetylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 90919alpha-Methyl-4-pyridinemethanolYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (310.0 mg; 8.25 mmol) was added portionwise to a cooled (0° C.) solution of 4-acetylpyridine (500.0 mg; 4.13 mmol) in ethanol under argon atmosphere. The reaction mixture was slowly warmed to room temperature, stirred for 4 hours. Quenched with water and solvent removed. Extracted with dichloromethane, washed with water, brine, dried and solvent removed to yield 500 milligrams of 1-(4-pyridyl)ethanol.

Workup

  1. customQuenched with water and solvent
  2. customremoved
  3. extractionExtracted with dichloromethane
  4. washwashed with water, brine
  5. customdried
  6. customsolvent removed

Sources & evidence

ORD record
ord-9d3975a245564ef98d27b4280dd45620
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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