Ammonium Hydroxide → 2-Tert-butylpyridin-4(1H)-one

HRID 2370364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370364
[C:1]([C:5]1O[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+:13]>>[C:1]([C:5]1[NH:13][CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 14923Ammonium HydroxideHCID 592936742-tert-butyl-4H-pyran-4-one

Produkt 1

HCID 582800252-Tert-butylpyridin-4(1H)-one

Versuchsvorschrift

A mixture of 2-tert-butyl-pyran-4-one (Step 1.6) (5.74 g, 37.7 mmol) and a 30% aqueous solution of ammonium hydroxide (100 mL) is stirred for 1 h at reflux, allowed to cool and concentrated. The residue is triturated with MeOH (200 mL) and filtered. The filtrate is concentrated and the residue purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1→92:7:1) to afford 4.46 g of the title compound as a yellow solid: ESI-MS: 152.0 [M+H]+; tR=1.45 min (System 1); TLC: Rf=0.11 (DCM/MeOH, 9:1).

Aufarbeitung

  1. temperatureat reflux
  2. temperatureto cool
  3. concentrationconcentrated
  4. customThe residue is triturated with MeOH (200 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1→92:7:1)

Quellen und Nachweise

ORD-Eintrag
ord-b141c3fe3c6343b8ada09866114c1dcc
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710085B2

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