반응 #42478

반응 방정식

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

borane dimethylsulfide

→

title compound

수율 45.8%

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

수율 45.8%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the resulting mixture was refluxed for 24 h
2. 2
   기타quenched with methanol
3. 3
   기타the solvent was removed under reduced pressure
4. 4
   기타Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

실험 절차

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.

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