反应 #56745

反应方程式

hydroxylamine hydrochloride

ethanol pyridine

1-[(3S)-5-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone

→

title compound

1-[5-Hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone oxime

溶剂

ethanol

反应条件

后处理

1. 1
   温度It was then heated
2. 2
   温度to reflux under nitrogen for 5 hours
3. 3
   温度Upon cooling
4. 4
   其他the solvent was removed
5. 5
   洗涤The solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
6. 6
   干燥dried over magnesium sulfate
7. 7
   过滤filtered
8. 8
   其他evaporated in vacuum

实验过程

A solution of hydroxylamine hydrochloride (2.38 g, 34.2 mmole) in 1:1 ethanol/pyridine (100 mL) was added to a solution of 1-[(3S)-5-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone (1.92 g, 8.57 mmole) in ethanol (200 mL). It was then heated to reflux under nitrogen for 5 hours. Upon cooling, the solvent was removed and replaced with ethyl acetate. The solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuum to give 1.89 g (93%) of the (S)-enantiomer of the title compound as a gray solid, m.p. 162° C., MS (ESI) m/z 240 (M+H)+.

来源