Реакция #42464

Уравнение реакции

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

potassium carbonate

bromobutane

→

title compound

Выход 72.6%

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

Выход 72.6%

Растворители

—

ethyl acetate hexanes

water

DMSO

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled to room temperature
2. 2
   Другоеseparated
3. 3
   ПромывкаThe organic layer was washed with water, and brine
4. 4
   Сушкаdried (magnesium sulfate)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеPurification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes)

Методика

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.

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