Methanol → alpha-Methyl-2-pyridinemethanol

HRID 230778Notes

Reaction equation

HRID 230778 reaction equation
CO.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10].[BH4-].[Na+]>O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([OH:11])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 142862-AcetylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 86784alpha-Methyl-2-pyridinemethanolYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol solution (100 mL) of 1-pyridin-2-ylethanone (10.0 g) was cooled to 0° C., sodium borohydride (6.2 g) was added thereto and stirred at that temperature for 4 hours. Then water was added to the reaction solution, and the organic solvent was evaporated off under reduced pressure. The resulting residue was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1 to 3/2) to obtain the entitled compound (9.0 g).

Workup

  1. customthe organic solvent was evaporated off under reduced pressure
  2. extractionThe resulting residue was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated off under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1 to 3/2)

Sources & evidence

ORD record
ord-971f629345c146689a8e5e3f7eccb98a
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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