反応 #42478

反応方程式

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

borane dimethylsulfide

→

title compound

収率 45.8%

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

収率 45.8%

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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.

出典