تفاعل #155398

معادلة التفاعل

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

ammonium chloride

sodium azide

→

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

المردود 69.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled to room temperature
2. 2
   أخرىwas partitioned between water and ether/hexanes (1:1 v/v)
3. 3
   أخرىThe phases were separated
4. 4
   غسيلthe organic phase was washed once each with water, brine
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated to an oil, which
8. 8
   أخرىwas purified by flash chromatography (silica gel/hexanes:10% ethyl acetate)

الإجراء التجريبي

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.

المصدر