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

HRID 444864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444864
[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-790fd20139324960b0f42d7c39867171
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476268B2

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