Triethylamine → Methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone

HRID 359315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359315
[Br-].[CH3:2][C:3]([CH3:15])=[CH:4][CH2:5][N+:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:14])[CH3:13])[CH:7]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[CH3:2][CH:3]([CH3:15])[CH:4]=[CH:5][N:6]1[CH2:11][CH2:10][CH2:9][C:8]([C:12]([CH3:13])=[O:14])=[CH:7]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 189633631-(3-Methyl-2-butenyl)-3-acetyl-pyridinium bromideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 53639438Methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1-(3-methyl-2-butenyl)-3-acetyl-pyridinium bromide (27.0 g, 0.1 mole) and triethylamine (10.1 g, 0.1 mole) in ethyl alcohol (50 ml) over 5% palladium on carbon (5 g) was hydrogenated at room temperature and pressure until two molar equivalents of hydrogen was taken up. The catalyst was removed by filtration and the filtrate concentrated at reduced pressure. The semi-solid residue was diluted with diethyl ether (75 ml), the solid removed by filtration and the filtrate concentrated under reduced pressure to leave a pale oil which solidified on standing. Recrystallisation from ethanol/water gave the product, methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone (4) as a pale yellow crystalline solid m.p 76-78°C.

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated at reduced pressure
  4. additionThe semi-solid residue was diluted with diethyl ether (75 ml)
  5. customthe solid removed by filtration
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto leave a pale oil which
  8. customRecrystallisation from ethanol/water

Quellen und Nachweise

ORD-Eintrag
ord-1d75396f0e574652aa12d434a6591622
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05000946

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