Reacción #792199

Ecuación de reacción

2-diazo-1-(furan-2-yl)ethanone

3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione

→

furan-2-yl(4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)methanone

Rendimiento 16.4%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed vigorously for 6 hours
2. 2
   OtroThe solvent was evaporated to dryness
3. 3
   workup.ADDITIONa mixture of two compounds, which
4. 4
   Otrowere separated by column chromatography
5. 5
   OtroCrystallization from acetone

Procedimiento

2-diazo-1-(furan-2-yl)ethanone (900 mg, 6.61 mmol) and 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione (846 mg, 10.05 mmol) were combined in dry benzene (10 ml) and refluxed vigorously for 6 hours. The solvent was evaporated to dryness, and the resulting crude material was subjected to column chromatography using 100-200 mesh range silica gel and an ethyl acetate/hexane solvent system. The crude material was a mixture of two compounds, which were separated by column chromatography. Crystallization from acetone yielded furan-2-yl(4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)methanone as a yellow solid (200 mg, 16.4%).

Fuente