Reacción #42464

Ecuación de reacción

Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

potassium carbonate

bromobutane

→

title compound

Rendimiento 72.6%

Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Rendimiento 72.6%

Disolventes

—

ethyl acetate hexanes

water

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to room temperature
2. 2
   Otroseparated
3. 3
   LavadoThe organic layer was washed with water, and brine
4. 4
   Secadodried (magnesium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroPurification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes)

Procedimiento

To a solution of Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (2.64 g) and potassium carbonate (5 g) in DMSO (20 mL) was added bromobutane (5 g), and the reaction mixture was stirred for 1 h at 80° C. The mixture was cooled to room temperature, diluted with 1:1 ethyl acetate/hexanes (100 mL) and water (160 mL), and separated. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes) afforded 2.24 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 8.13, 7.63, 4.74, 3.96, 3.92, 1.64, 1.42, 0.97.

Fuente