반응 #42464

반응 방정식

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

potassium carbonate

bromobutane

→

title compound

수율 72.6%

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

수율 72.6%

용매

—

ethyl acetate hexanes

water

DMSO

반응 조건

후처리

1. 1
   온도The mixture was cooled to room temperature
2. 2
   기타separated
3. 3
   세척The organic layer was washed with water, and brine
4. 4
   건조dried (magnesium sulfate)
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by flash column chromatography (silica, 1:10 ethyl acetate/hexanes)

실험 절차

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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