Ethyl Acetate → alpha-Methyl-3-pyridinemethanol

HRID 1186322Notes

Reaction equation

HRID 1186322 reaction equation
C[Mg]Br.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=1.[Cl-].[NH4+].[C:14](OCC)(=O)C>O1CCCC1>[OH:11][CH:10]([C:6]1[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 101192alpha-Methyl-3-pyridinemethanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To methylmagnesium bromide (a 0.96 mol/L solution in tetrahydrofuran, 16.6 mL, 15.9 mmol), a solution of 3-pyridinecarboxaldehyde (500 μL, 5.30 mmol) in tetrahydrofuran (5.0 mL) was slowly added under a nitrogen atmosphere at 0° C., and the mixture was stirred at the same temperature for 1. Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol 9/1) to give 3-(1-hydroxyethyl)pyridine (Compound CA) (498 mg, yield: 76%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol 9/1)

Sources & evidence

ORD record
ord-e24527e5a60c4647a66d1aea74704067
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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