反应 #42465

反应方程式

Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

9-BBN

ethanolamine

→

title compound

收率 91.5%

Methyl 4-butyl-8-iodo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

收率 91.5%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   温度at reflux for 1.5 h
2. 2
   浓缩the resulting solution was concentrated under reduced pressure
3. 3
   洗涤The residue was washed with hexanes
4. 4
   过滤filtered
5. 5
   浓缩the filtrate was concentrated under reduced pressure
6. 6
   其他Purification by flash column chromatography (silica, 10% ethyl acetate/hexanes)

实验过程

A solution of Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (680 mg) and 9-BBN (900 mg) in tetrahydrofuran (30 mL) was heated at reflux for 1.5 h. The mixture was cooled to room temperature, ethanolamine (0.22 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, 10% ethyl acetate/hexanes) afforded 600 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.75, 7.28, 4.34, 3.86, 3.36, 3.28, 1.58, 1.40, 0.96.

来源