Sodium hydride → 8-(2-Chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

HRID 4306

Reaktionsgleichung

Reaktionsgleichung von HRID 4306
[H-].[Na+].[I-].[Cl:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][N+](C)(C)C)=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1>C(O)C#C>[Cl:4][C:5]1[CH:27]=[CH:26][CH:25]=[CH:24][C:6]=1[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][O:8][CH2:7][C:6]#[CH:5])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 138259378-(2-Chlorobenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide

Produkt 1

HCID 138259178-(2-Chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridineAusbeute 124,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7859Propargyl alcoholLösungsmittel

Versuchsvorschrift

To a solution of sodium hydride (60% in mineral oil dispersion, 0.186 g) in 2-propynyl alcohol (8 ml) was added 8-(2-chlorobenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (2 g) and the mixture was heated at 90°-95° C. with stirring for 1 hour. After being cooled, the mixture was poured into ice-water and the resulting precipitate was collected by filtration and dissolved in methylene chloride. The solution was treated successively with silica gel (1 g) and activated charcoal and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of methylene chloride and n-hexane to give 8-(2-chlorobenzyloxy)-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (0.9 g).

Aufarbeitung

  1. temperaturethe mixture was heated at 90°-95° C.
  2. temperatureAfter being cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutiondissolved in methylene chloride
  5. additionThe solution was treated successively with silica gel (1 g) and activated charcoal
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of methylene chloride and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b00092430ac54cc19a9bd1a0f1697fff
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725601

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