Tetrabutylammonium Fluoride → 2-Ethenylpiperidin-4-one

HRID 1510158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510158
[O:1]=[C:2]1[CH2:7][CH2:6][N:5](C(OCC[Si](C)(C)C)=O)[CH:4]([CH:17]=[CH2:18])[CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH:17]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:7][CH2:6][NH:5]1)=[CH2:18]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 667904002-(Trimethylsilyl)ethyl 4-oxo-2-vinylpiperidine-1-carboxylate

Produkt 1

HCID 205693092-Ethenylpiperidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(trimethylsilyl)ethyl 4-oxo-2-vinylpiperidine-1-carboxylate (24.1 g, 89.0 mmol) was dissolved in tetrahydrofuran (90 ml) at 0° C. and added TBAF (268 ml, 268 mmol) dropwise. The solution stirred at 0° C. for 30 min then at rt for an additional three hrs. The solution was quenched with 1N HCl and extracted five times with EtOAc. The organic fractions were combined, dried with Na2SO4, and concentrated. The crude product was not purified.

Aufarbeitung

  1. waitat rt for an additional three hrs
  2. customThe solution was quenched with 1N HCl
  3. extractionextracted five times with EtOAc
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was not purified

Quellen und Nachweise

ORD-Eintrag
ord-fbf73bb80b2548a88a9662d0c6031966
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211904B2

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