反应 #42478

反应方程式

methyl 4-butyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

borane dimethylsulfide

→

title compound

收率 45.8%

Methyl 4-butyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

收率 45.8%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   温度the resulting mixture was refluxed for 24 h
2. 2
   其他quenched with methanol
3. 3
   其他the solvent was removed under reduced pressure
4. 4
   其他Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

实验过程

To an ice-cold, stirred solution of methyl 4-butyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (840 mg) in tetrahydrofuran (32 mL) was added borane dimethylsulfide complex (3.2 mL, 2.0 M tetrahydrofuran) and the resulting mixture was refluxed for 24 h. The mixture was cooled to room temperature, quenched with methanol, and the solvent was removed under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided 364 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.27, 7.22, 6.41, 3.84, 3.47-3.45, 3.32-3.23, 1.60-1.58, 1.42-1.37, 0.99-0.94.

来源