Ethyl Acetate → 2-(Pyridin-3-yl)propan-2-ol

HRID 1186354Notes

Reaction equation

HRID 1186354 reaction equation
C[Mg]Br.[C:4]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)(=[O:6])[CH3:5].[Cl-].[NH4+].[C:15](OCC)(=O)C>O1CCCC1>[OH:6][C:4]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)([CH3:15])[CH3:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 95893-AcetylpyridineHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 107254032-(Pyridin-3-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To methylmagnesium bromide (a 0.96 mol/L solution in tetrahydrofuran, 6.26 mL, 5.97 mmol), a solution of 3-acetylpyridine (362 mg, 2.99 mmol) in tetrahydrofuran (3.6 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 thereby 3-(1-hydroxy-1-methylethyl)pyridine (Compound DG) (415 mg, yield: quantitative) was obtained.

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-9d93b4c14a4a40478e6c813c0675fa68
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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