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

HRID 27039

Reaction equation

HRID 27039 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-6783eeea9c804d0b933662c82c1126bf
Source dataset
uspto-grants-1980_09
Patent number
US04220577

Linked notes

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