Reacción #155398

Ecuación de reacción

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

ammonium chloride

sodium azide

→

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

Rendimiento 69.1%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled to room temperature
2. 2
   Otrowas partitioned between water and ether/hexanes (1:1 v/v)
3. 3
   OtroThe phases were separated
4. 4
   Lavadothe organic phase was washed once each with water, brine
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated to an oil, which
8. 8
   Otrowas purified by flash chromatography (silica gel/hexanes:10% ethyl acetate)

Procedimiento

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.

Fuente