Реакция #155398

Уравнение реакции

Ethyl-(2R)-2,3-epoxyproprionate

ammonium chloride

sodium azide

→

(R)-ethyl-3-azido-2-hydroxypropionate

Выход 69.1%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was cooled to room temperature
2. 2
   Другоеwas partitioned between water and ether/hexanes (1:1 v/v)
3. 3
   ДругоеThe phases were separated
4. 4
   Промывкаthe organic phase was washed once each with water, brine
5. 5
   Сушкаdried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated to an oil, which
8. 8
   Другоеwas purified by flash chromatography (silica gel/hexanes:10% ethyl acetate)

Методика

Ethyl-(2R)-2,3-epoxyproprionate (0.5 g, 4.3 mmol), ammonium chloride (0.253 g, 4.73 mmol), and sodium azide (0.336 g, 5.17 mmol) were combined in DMF (8 mL), and the mixture was heated at 75° C. for 14 hours. The reaction was cooled to room temperature, and was partitioned between water and ether/hexanes (1:1 v/v). The phases were separated, and the organic phase was washed once each with water, brine, dried over MgSO4, filtered, and concentrated to an oil, which was purified by flash chromatography (silica gel/hexanes:10% ethyl acetate) to give (R)-ethyl-3-azido-2-hydroxypropionate as a clear oil (0.47 g, 2.97 mmol, 69% yield). Rf 0.27 (hexanes: 10% EtOAc, v/v, p-anisaldehyde); MS m/e [M+Na]+ calcd 182.1. found 182.0.

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