3-Acetyl-6-methylpyridine → 1-(6-Methylpyridin-3-yl)ethan-1-ol

HRID 1922294

Reaction equation

HRID 1922294 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 952923-Acetyl-6-methylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 101299891-(6-Methylpyridin-3-yl)ethan-1-olYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 1-(6-methyl-3-pyridinyl)ethanone (1.0 g, 7.4 mmol) in absolute ethanol (10 ml) at 0° C. was added sodium borohydride (0.14 g, 3.7 mmol) portionwise over 20 minutes. The reaction mixture was stirred at 0° C. for 1.5 hours before warming to room temperature. The mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulphate, filtered, and evaporated in vacuo to give the crude product 1-(6-methyl-3-pyridinyl)ethanol (810 mg).

Workup

  1. temperaturebefore warming to room temperature
  2. customThe mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-33d182ab243f429f93c23547167915af
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Linked notes

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