反応 #42464

反応方程式

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

potassium carbonate

bromobutane

→

title compound

収率 72.6%

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

収率 72.6%

溶媒

—

ethyl acetate hexanes

water

DMSO

反応条件

後処理

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

実験手順

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.

出典