反应 #42496

反应方程式

methyl 4-butyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

9-BBN

ethanolamine

→

title compound

收率 80.1%

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

收率 80.1%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   浓缩the resulting solution was concentrated under reduced pressure
2. 2
   洗涤The residue was washed with hexanes
3. 3
   过滤filtered
4. 4
   浓缩the filtrate was concentrated under reduced pressure
5. 5
   其他Purification by flash column chromatography (silica, 25% ethyl acetate/hexanes)

实验过程

A solution of methyl 4-butyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (800 mg) and 9-BBN (1.6 g) in tetrahydrofuran (13 mL) was refluxed for 1.5 h. The mixture was cooled to room temperature, ethanolamine (0.4 mL) was added, and the resulting solution was concentrated under reduced pressure. The residue was washed with hexanes, filtered, and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica, 25% ethyl acetate/hexanes) afforded 607 mg of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.21, 7.16, 6.75, 4.24-4.21, 3.78, 3.34-3.24, 1.55-1.47, 1.38-1.30, 0.95-0.90.

来源