반응 #1835688

반응 방정식

water

p-Toluenesulfonylmethylisocyanide

1,4-cyclohexanedione monoethyleneketal

potassium tert-butoxide

→

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

수율 72.0%

용매

1,2-dimethoxyethane

ethanol

반응 조건

후처리

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

실험 절차

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.

출처