Reaktion #1065123

Reaktionsgleichung

Sodium hydride

1-benzyl-2,4-dioxopiperidine

2-methylthio-1,3-dithiolium iodide

→

1-benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

Ausbeute 87.8%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction mixture is poured onto water
2. 2
   Extraktionextracted with chloroform
3. 3
   WaschenThe extract is washed with a saturated sodium chloride solution
4. 4
   Sonstigedried
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Sonstigeto remove the solvent
7. 7
   SonstigeThe residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1)
8. 8
   Sonstigerecrystallized from isopropyl alcohol

Vorschrift

Sodium hydride (60% dispersion in oil) (80 mg) is suspended in tetrahydrofuran (10 ml), and thereto are added 1-benzyl-2,4-dioxopiperidine (200 mg) and 2-methylthio-1,3-dithiolium iodide (273 mg). The mixture is stirred at room temperature for 30 minutes. The reaction mixture is poured onto water and extracted with chloroform. The extract is washed with a saturated sodium chloride solution, dried and then distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1) and recrystallized from isopropyl alcohol to give 1-benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (262 mg, 87.8%) as pale yellow needles, m.p. 122°-124° C.

Quelle