Sodium Hydroxide → 8-(2-Methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridine

HRID 4303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4303
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([CH:16]=[C:17]=[CH2:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 138258948-(2-Methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 138259148-(2-Methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridineAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 8-(2-methylbenzyloxy)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.99 g) and 1N-sodium hydroxide solution (5.65 ml) in methanol (50 ml) was stirred for 72 hours at room temperature. The mixture was evaporated in vacuo and the residue was dissolved in chloroform. The solution was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (14 g) with a mixture of chloroform and ethyl acetate (15:1) as an eluent to give 8-(2-methylbenzyloxy)-3-(1,2-propadienyl)-2-methylimidazo[1,2-a]pyridine (0.27 g).

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (14 g) with a mixture of chloroform and ethyl acetate (15:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-ebc91131d5f547cb8a0bb15bdb77240c
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725601

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