反応 #155398

反応方程式

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

ammonium chloride

sodium azide

→

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

収率 69.1%

溶媒

DMF

反応条件

後処理

1. 1
   温度The reaction was cooled to room temperature
2. 2
   その他was partitioned between water and ether/hexanes (1:1 v/v)
3. 3
   その他The phases were separated
4. 4
   洗浄the organic phase was washed once each with water, brine
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated to an oil, which
8. 8
   その他was purified by flash chromatography (silica gel/hexanes:10% ethyl acetate)

実験手順

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.

出典