2-Acetylpyridine → alpha-Methyl-2-pyridinemethanol

HRID 1364398Notes

Reaction equation

HRID 1364398 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:5])[CH3:4]>CO>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:3]([OH:5])[CH3:4]

Participants

4

Reactant 2

HCID 142862-AcetylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 86784alpha-Methyl-2-pyridinemethanolYield 12.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (344 mg; 9.08 mmol) was added portionwise to a solution of 2-acetylpyridine (500.0 mg; 8.25 mmol) in methanol. The reaction mixture was stirred overnight at room temperature. Quenched with water and extracted with ethyl acetate and solvent removed to yield 125 milligrams of 1-(2-pyridyl)ethanol.

Workup

  1. customQuenched with water
  2. extractionextracted with ethyl acetate and solvent
  3. customremoved

Sources & evidence

ORD record
ord-c056e7153591491da57e2c6aecf477ff
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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