Tetrabutylammonium Fluoride → HCID 22496024, Verbindung

HRID 1816007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816007
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:43][Si](C(C)(C)C)(C)C)([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)C#N)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[O:43])=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 22496050HCID 22496050, Verbindung

Produkt 1

HCID 22496024HCID 22496024, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of TBAF in THF (1.0 M, 2.2 mL, 2.2 mmole) was added dropwise to a solution of (±)-3-(4-benzyloxyphenyl)-2-(ter-butyldimethylsilyloxy)-2-(pyridin-3-yl)propionitrile (769 mg, 1.73 mmole) in dry THF (10 mL) at −15° C. After 30 min, the reaction was partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with H2O, dried (MgSO4), filtered through a plug of silica gel, and concentrated to afford impure title compound (492 mg, 94%) as a yellow solid: MS (ES) m/e 304 (M+H)+. This material was used without further purification.

Aufarbeitung

  1. customthe reaction was partitioned between EtOAc and H2O
  2. customThe layers were separated
  3. washthe organic layer was washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8590528ae1ec47899148221c54bfa954
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06881736B1

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