Ammonium Chloride → 1-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one

HRID 1454964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454964
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[C:11][Si](C)(C)C)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[CH:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 575312291-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

Produkt 1

HCID 575312331-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)but-3-yn-2-oneAusbeute 132 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-(6-chloropyridazin-3-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one (9.6 g, 26.4 mmol) in THF (200 mL) was added TBAF (32.9 mL, 32.9 mmol) at 0° C. After stirring at 0° C. for 15 min, the reaction was poured into aqueous NH4Cl, and extracted with EtOAc. The combined organic layers were washed with 1N HCl, brine, dried over MgSO4, and concentrated to an oil. The crude product was purified by silica gel chromatography (hexanes/CH2Cl2) to give title compound (10.2 g).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with 1N HCl, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified by silica gel chromatography (hexanes/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-2569b45983884ea38e166400524385bf
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482345B2

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