反応 #56745

反応方程式

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

溶媒

ethanol

反応条件

後処理

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
   その他the solvent was removed
5. 5
   洗浄The solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   その他evaporated in vacuum

実験手順

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)+.

出典