Reaktion #1835688

Reaktionsgleichung

water

p-Toluenesulfonylmethylisocyanide

1,4-cyclohexanedione monoethyleneketal

potassium tert-butoxide

→

1,4-dioxaspiro[4,5]decane-8-carbonitrile

Ausbeute 72.0%

Lösungsmittel

1,2-dimethoxyethane

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionextracted with ethyl acetate three times
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Vorschrift

p-Toluenesulfonylmethylisocyanide (27.0 g) was added at room temperature to a solution of 1,4-cyclohexanedione monoethyleneketal (16.6 g) in 1,2-dimethoxyethane (133 ml) and ethanol (13 ml). Then, potassium tert-butoxide was added under ice cooling over an hour, and stirred at room temperature for three hours. After completion of the reaction, water was added and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1,4-dioxaspiro[4,5]decane-8-carbonitrile (12.8 g) as a colorless oil.

Quelle