Water → 8-(2-Ethyl-6-methylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine

HRID 1386079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386079
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:30][CH3:31])[C:15]2=[N:14][C:13]=1[CH3:32])(OCC)=[O:8].O.[OH-].[Na+]>O1CCCC1>[CH2:30]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[CH2:22][O:21][C:20]1[C:15]2[N:16]([C:12]([CH2:7][OH:8])=[C:13]([CH3:32])[N:14]=2)[CH:17]=[CH:18][CH:19]=1)[CH3:31]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 217173563-Carboethoxy-8-(2-ethyl-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 217173318-(2-Ethyl-6-methylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of LiAlH4 (0.08 g, 2.1 mmol) in tetrahydrofuran (25 ml) was added 3-carboethoxy-8-(2-ethyl-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine (1.0 g, 2.8 mmol) in tetrahydrofuran (25 ml). After stirring the mixture at room temperature for 2 h., 0.2 ml of water was added dropwise, followed by 0.2 ml of 15% sodium hydroxide and then 0.6 ml of water. The solids were removed by filtration and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Crystallization from diethyl ether gave 0.52 g (60%) of the title compound.

Aufarbeitung

  1. customThe solids were removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. customCrystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-58fd5db54c6d4484986cbad8df23fc98
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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