Reaktion #433044

Reaktionsgleichung

(4-fluoro)-1-benzoyl-1-cyanocyclopropane

trimethylsulphoxonium iodide

sodium hydride

1,2,4-triazole

hydrogen

→

1-(1-cyanocyclopropyl)-1-(4-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanol

Lösungsmittel

DMSO

DMSO

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred for 2 h at 50° C. and for 4 h at 80° C.
2. 2
   Extraktionextracted
3. 3
   WaschenThe organic phase is washed with 2N sodium hydroxide solution
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue is chromatographed on silica gel
7. 7
   Sonstigethe product is crystallized from diethyl ether

Vorschrift

2.42 g (11 mmol) of trimethylsulphoxonium iodide (EGA) are added in portions at 20° C. to a suspension of 0.33 g (11 mmol) of sodium hydride (80% in oil) in 20 ml of DMSO p.a. The mixture is stirred until evolution of hydrogen has ended and 2 g (10mmol) of (4-fluoro)-1-benzoyl-1-cyanocyclopropane, dissolved in 5 ml of abs. DMSO, are rapidly added dropwise. The mixture is stirred for 1 h at RT and for 1 h at 40° C., then 1.04 g (15 mmol) of 1,2,4-triazole (sublimed) and 0.46 g (5 mmol) of 1,2,4-triazole Na salt in DMSO are added. The mixture is stirred for 2 h at 50° C. and for 4 h at 80° C., poured into ice-water and extracted using dichloromethane. The organic phase is washed with 2N sodium hydroxide solution, dried over Na2SO4 and concentrated. The residue is chromatographed on silica gel and the product is crystallized from diethyl ether. 1.2 g (44% of theory) of colorless crystals of 1-(1-cyanocyclopropyl)-1-(4-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanol are thus obtained having a melting point of 121°-122° C.,

Quelle