반응 #155398

반응 방정식

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

ammonium chloride

sodium azide

→

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

수율 69.1%

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction was cooled to room temperature
2. 2
   기타was partitioned between water and ether/hexanes (1:1 v/v)
3. 3
   기타The phases were separated
4. 4
   세척the organic phase was washed once each with water, brine
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated to an oil, which
8. 8
   기타was purified by flash chromatography (silica gel/hexanes:10% ethyl acetate)

실험 절차

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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