3-Pyridinemethanol → 1,1-Dimethylethyl 2-(3-pyridinylmethoxy)acetate

HRID 1419686Notes

Reaction equation

HRID 1419686 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CN(C=O)C>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:4]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 247635281,1-Dimethylethyl 2-(3-pyridinylmethoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (0.4 g) in DMF (8 ml) was added dropwise a solution of 3-pyridinemethanol (1.09 g) in DMF (5 ml), and the mixture was stirred at room temperature for 30 minutes. Then a solution of tert-butyl bromoacetate (1.62 ml) in DMF (5 ml) was added to the mixture. After stirring for one hour, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in AcOEt (20 ml), washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified with SiO2 column chromatography (eluted with 1% MeOH in CHCl3) to give tert-butyl (3-pyridylmethoxy)acetate (435 mg) as an oil.

Workup

  1. stirringAfter stirring for one hour
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in AcOEt (20 ml)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with SiO2 column chromatography (eluted with 1% MeOH in CHCl3)

Sources & evidence

ORD record
ord-11700f33d1004d248ea0558298597146
Source dataset
uspto-grants-1999_03
Patent number
US05888972

Reaction notes

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