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

HRID 27039

Reaktionsgleichung

Reaktionsgleichung von HRID 27039
[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]

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 79713-HydroxypyridineHCID 10942334Sodium Methoxide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6783eeea9c804d0b933662c82c1126bf
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220577

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