反应 #42464

反应方程式

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

potassium carbonate

bromobutane

→

title compound

收率 72.6%

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

收率 72.6%

溶剂

—

ethyl acetate hexanes

water

DMSO

反应条件

后处理

1. 1
   温度The mixture was cooled to room temperature
2. 2
   其他separated
3. 3
   洗涤The organic layer was washed with water, and brine
4. 4
   干燥dried (magnesium sulfate)
5. 5
   过滤filtered
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他Purification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes)

实验过程

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.

来源