Isopropyl Acetate → HCID 16680143, Verbindung

HRID 968877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968877
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([C:28]2([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[F:42])[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(OC(C)C)(=O)C>O1CCCC1.O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([C:28]2([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[F:42])[CH2:29][CH2:30][C:31](=[CH:9][C:7]#[N:8])[CH2:32][CH2:33]2)(=[O:26])=[O:27])=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 7915Isopropyl AcetateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 104301374-(4-chlorophenyl)sulfonyl-4-(2,5-difluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 16680143HCID 16680143, VerbindungAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of potassium tert butoxide (1.0M in THF, 3.20 Kg, 3.55 mol) in tetrahydrofuran (2.1L) was added diethyl (cyanomethyl)phosphonate (642 g, 3.62 mol), maintaining the temperature below 5° C. The resulting solution was aged for 2 h and a solution of 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanone (1.07 Kg, 2.78 mol) (Preparation 2) in tetrahydrofuran (3.9 L) was added. After the reaction was completed, isopropyl acetate (13.1 L) and water (26.3 L) were added. The organic layer was washed with brine and then concentrated to 1 L. Heptane (10.5 L) was added. The resulting solid was filtered, washed with heptane, dried in vacuo at 37° C. and then slurried in diethyl ether (5 L). Filtration and drying in vacuo afforded 989 g (87% yield) of [4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylidene]acetonitrile. 1H NMR (CDCl3) 7.41-7.34 (4H, m), 7.25-7.06 (2H, m), 6.94-6.87 (1H, m), 5.12 (1H, s), 3.05-3.03 (1H, m), 2.92-2.86 (2H, m), 2.54-2.50 (1H, m), and 2.30-2.03 (4H, m).

Aufarbeitung

  1. temperaturemaintaining the temperature below 5° C
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated to 1 L
  4. additionHeptane (10.5 L) was added
  5. filtrationThe resulting solid was filtered
  6. washwashed with heptane
  7. customdried in vacuo at 37° C.
  8. filtrationFiltration
  9. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ecef6557fef14a458a1e4f772821e5bb
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304094B2

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