Ethyl Acetate → α-(1,1-Dimethylethyl)-3-pyridinemethanol

HRID 1186328Notes

Reaction equation

HRID 1186328 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[C:9]([Li])([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1.CCCCC>[CH3:10][C:9]([CH3:12])([CH3:11])[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[OH:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 322666α-(1,1-Dimethylethyl)-3-pyridinemethanolYield 18%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Pyridinecarboxaldehyde (200 μL, 2.12 mmol) was dissolved in tetrahydrofuran (5.0 mL). To this, tert-butyllithium (a 1.46 mol/L solution in pentane, 4.37 mL, 6.36 mmol) was added dropwise 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, hexane/ethyl acetate=1/1) to give 3-(2,2-dimethyl-1-hydroxypropyl)pyridine (Compound CG) (64.0 mg, yield: 18%).

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, hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-800644b7ff474971acd8d93cf1b79195
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…