Water → 3,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone

HRID 465453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465453
S(=O)(=O)(O)O.C1CO[C:8]([CH3:24])([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([C:21](=O)[CH3:22])[CH2:17][CH2:18][C:19]#[N:20])=[CH:12][CH:11]=2)[O:7]1.[OH2:27]>C(O)(=O)C>[CH2:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]=2[CH3:22])=[CH:12][CH:11]=1)[C:8]([CH3:24])=[O:7]

Komponenten

5

Edukt 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 198745084-(4-(2,2-(Ethylenedioxy)propyl)phenyl)-5-oxo-hexane nitrile

Produkt 1

HCID 198745593,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Concentrated sulphuric acid (5 ml) was added dropwise to a solution of 4-(4-(2,2-(ethylenedioxy)propyl)phenyl)-5-oxo-hexane nitrile (3.09 g) in glacial acetic acid (21 ml). The orange solution was allowed to stand at room temperature for 3 days then poured into water and allowed to stand for 2 hr. The solution was extracted with chloroform, the organic layer separated, washed with sodium bicarbonate solution, dried (MgSO4) and evaporated to an oil (2.44 g) which was chromatographed on silica. Elution with chloroform gave 3,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone as an oil.

Aufarbeitung

  1. waitto stand for 2 hr
  2. extractionThe solution was extracted with chloroform
  3. customthe organic layer separated
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil (2.44 g) which
  7. customwas chromatographed on silica
  8. washElution with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-7d261a97cc6a449e9da15e230b0d5ba5
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153210

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