Reacción #80737

Ecuación de reacción

indoline

triethylamine

ethyl chlorooxalate

→

N-ethoxalylindoline

Rendimiento 108.6%

Disolventes

dichloromethane

Brine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITfor 1 h at room temperature
2. 2
   Otroorganic layer was separated
3. 3
   LavadoThe organic layer was washed with diluted aqueous hydrochloric acid and successively brine
4. 4
   Secadodried over magnesium sulfate
5. 5
   Concentraciónconcentrated

Procedimiento

To a solution of indoline (2.0 g, 16.8 mmol) and triethylamine (5 mL) in dichloromethane (30 mL) was added slowly ethyl chlorooxalate (2.3 mL, 20.1 mmol) at 0° C. The mixture was stirred for 10 min at 0° C. and then for 1 h at room temperature. Brine was added and organic layer was separated. The organic layer was washed with diluted aqueous hydrochloric acid and successively brine, dried over magnesium sulfate, and concentrated to give 4.0 g of N-ethoxalylindoline (100%): 1H NMR (270 MHz, CDCl3) δ8.18 (dd, 1H, J=8, 1 Hz), 7.22 (m, 2H), 7.10 (dd, 1H, J=8, 1 Hz), 4.38 (q, 2H, J=7 Hz), 4.22 (t, 2H, J=8 Hz), 3.20 (t, 2H, J=8 Hz), 1.40 (t, 3H, J=7 Hz).

Fuente