Sodium Azide → Ethyl 3-azido-2-hydroxypropanoate

HRID 1453836노트

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HRID 1453836 반응식
Br[CH2:2][CH:3]([OH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:10]=[N+:11]=[N-:12].[Na+]>CCO.O>[N:10]([CH2:2][CH:3]([OH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N+:11]=[N-:12]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 13180684Ethyl 3-bromo-2-hydroxypropanoate

생성물 1

HCID 10888191Ethyl 3-azido-2-hydroxypropanoate

시약·촉매·용매 1

HCID 19096565Water ethanol용매

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온도
90 °C

실험 절차

To a solution of ethyl 3-bromo-2-hydroxypropanoate (22.1 g, 112.0 mmol) in EtOH/H2O (1:1) was added sodium azide (10.9 g, 168.0 mmol). The reaction was stirred and heated to 90° C. for 3 days. The EtOH was removed in vacuo and the remaining aqueous solution was extracted with CHCl3 several times. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford the azide as an orange oil. 1H NMR (400 MHz, d6-DMSO) δ 5.96 (d, J=5.6 Hz, 1H), 4.31-4.28 (m, 1H), 4.19-4.08 (m, 2H), 3.51-3.40 (m, 2H), 1.28-1.17 (m, 3H).

후처리

  1. customThe EtOH was removed in vacuo
  2. extractionthe remaining aqueous solution was extracted with CHCl3 several times
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b2e2702fe4a14ab487c9f275c9e007fd
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476666B2

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