Propargyl bromide → 3-(Prop-2-ynyloxy)pyridine

HRID 426652Notes

Reaction equation

HRID 426652 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].[CH2:11](Br)[C:12]#[CH:13]>CN(C)C=O>[CH2:13]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:12]#[CH:11]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 79713-HydroxypyridineHCID 10942334Sodium Methoxide

Product 1

HCID 114236223-(Prop-2-ynyloxy)pyridineYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 9.5 g (0.1 mole) 3-hydroxypyridine, 5.2 g (0.1 mole) sodium methylate and 150 ml N,N-dimethylformamide, there was added 12.0 g (0.1 mole) propargyl bromide at room temperature over a two hour period. Most of the solvent was removed under reduced pressure. The residue was taken up with 200 ml methylene chloride and 100 ml water, the layers were separated and the methylene chloride evaporated to give 4.5 g 3-(2-propynyloxy)pyridine, yield 34%.

Workup

  1. customMost of the solvent was removed under reduced pressure
  2. customthe layers were separated
  3. customthe methylene chloride evaporated

Sources & evidence

ORD record
ord-57d42ac7cd074a47b9ad814fc808f535
Source dataset
uspto-grants-1979_10
Patent number
US04170704

Reaction notes

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