Реакция #56745

Уравнение реакции

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

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ТемператураIt was then heated
2. 2
   Температураto reflux under nitrogen for 5 hours
3. 3
   ТемператураUpon cooling
4. 4
   Другоеthe solvent was removed
5. 5
   ПромывкаThe solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated in vacuum

Методика

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)+.

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