Cesium fluoride → 4-(p-Chlorophenyl)-3-fluoro-4-methyl-2-pentenenitrile

HRID 610848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610848
[F-:1].[Cs+].F.[K].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:18])([CH3:17])[C:13]#[C:14][C:15]#[N:16])=[CH:8][CH:7]=1.C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([CH3:18])([CH3:17])[C:13]([F:1])=[CH:14][C:15]#[N:16])=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 25953Cesium fluorideHCID 21226206Ethyl acetate hexaneHCID 219955344-(p-Chlorophenyl)-4-methyl-2-pentynenitrileHCID 53443437Potassium fluoride, 99%, spray-dried

Produkt 1

HCID 542690284-(p-Chlorophenyl)-3-fluoro-4-methyl-2-pentenenitrileAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of cesium fluoride (41.38 g, 0.272 mol), potassium hydrogen fluoride (10.64 g, 0.136 mol) and water (13.07 g, 0.726 mol) in N,N-dimethylformamide is stirred for 10 minutes, treated with a solution of 4-(p-chlorophenyl)-4-methyl-2-pentynenitrile (18.5 g, 0.091 mol) in N,N-dimethylformamide, stirred at 80-85° C. for 4 hours, stirred at room temperature overnight and diluted with water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and a 1:9 ethyl acetate/hexane solution gives the title product as an oil (15.6 g, 76.8% yield).

Aufarbeitung

  1. stirringstirred at 80-85° C. for 4 hours
  2. stirringstirred at room temperature overnight
  3. extractionThe aqueous mixture is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Quellen und Nachweise

ORD-Eintrag
ord-2b0d60a93a304d6594dc6d994d7e9ec7
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998673

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