تفاعل #42478

معادلة التفاعل

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

borane dimethylsulfide

→

title compound

المردود 45.8%

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

المردود 45.8%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe resulting mixture was refluxed for 24 h
2. 2
   أخرىquenched with methanol
3. 3
   أخرىthe solvent was removed under reduced pressure
4. 4
   أخرىPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر