Reacción #6703

Ecuación de reacción

methanol

sodium hydride

Isatin

→

N-[4-(1,3-dioxolyl)phenyl]isatin

Disolventes

chloroform

chloroform

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThis suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours
2. 2
   TemperaturaIt was then cooled to room temperature
3. 3
   FiltraciónThe resulting suspension was filtered
4. 4
   Concentraciónthe filtrate was concentrated under reduced pressure
5. 5
   Otroevaporated to dryness
6. 6
   OtroA thick, viscous oil was recovered which
7. 7
   Otrosuch for the next reaction

Procedimiento

Isatin (1.88 g, 0.0128 mol) in anhydrous DMF (100 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (0.3 g, 1 equivalent). The reaction was warmed to room temperature and stirred for 1 hour. It was then treated with 2-(4-bromophenyl)-1,3-dioxalane (2.83 g, 0.0124 mol) followed by CuI (4.71 g, 2 equivalents). This suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. The resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in xylenes (100 mL) and evaporated to dryness. A thick, viscous oil was recovered which was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion, Rf (product)=0.91.

Fuente