Reacción #2439960

Ecuación de reacción

5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

trifluoroacetic acid

NaBH4

→

5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one

Rendimiento 61.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Otroforming a yellow foamy mixture
3. 3
   Temperaturato warm to room temperature, during which a tan solid
4. 4
   Otroprecipitated out of solution
5. 5
   FiltraciónThe tan solid was collected by filtration
6. 6
   Lavadowashed with water

Procedimiento

In a dried 250 mL round bottom flask, 20.73 mL of trifluoroacetic acid was added and then cooled to 0° C. under Ar(g). NaBH4 in pellet form (1.35 g, 35.71 mmol, ˜1.5 pellets) was added to the flask. 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 7, 1.0 g, 3.55 mmol) was then added in slowly over 15 min. After the addition was completed, the reaction was allowed to warm to room temperature and was stirred for 36 hours forming a yellow foamy mixture. The mixture was poured over ice-water and allowed to warm to room temperature, during which a tan solid precipitated out of solution. The tan solid was collected by filtration and washed with water affording 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one in 61% yield (0.589 g, 2.165 mmol).

Fuente