Réaction #578232

Équation de réaction

product

Diethyl 2-(3-(ethoxycarbonyl)-2,3-dihydrothiazol-2-yl)malonate

tetrachloro-1,2-benzoquinone

→

title compound

Diethyl 2-(thiazol-2(3H)-ylidene)malonate

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewas then washed with saturated aqueous sodium bicarbonate solution (200.0 ml) and brine (100.0 ml)
2. 2
   SéchageThe organic layer was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuum
5. 5
   Autrethe crude product was purified by flash column chromatography on silica gel

Mode opératoire

To a solution of the product of Example 44A (12.9 g, 40.7 mmoles) in dichloromethane (100.0 ml) was added tetrachloro-1,2-benzoquinone (10.0 g, 40.7 mmoles) in portions at about 0° C., such that the mixture always had time to decolorize to a yellow-orange color. The mixture was then stirred for about 1 hour at 0° C. and was then washed with saturated aqueous sodium bicarbonate solution (200.0 ml) and brine (100.0 ml). The organic layer was dried over MgSO4, filtered, concentrated in vacuum and the crude product was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide the title compound.

Source