반응 #2408

ord-fca1a49f76c14ce8bae2a93158f456ab

반응 방정식

O
water
OCCOc1cc(Cl)ncn1
2-(6-chloropyrimidin-4-yloxy)ethanol
[N-]=[N+]=[N-].[Na+]
sodium azide
[N-]=[N+]=Nc1cc(OCCO)ncn1
2-(6-azidopyrimidin-4-yloxy)ethanol
수율 28.9%

반응 조건

온도
70°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도After cooling
  2. 2
    추출extracted with ethyl acetate
  3. 3
    건조The ethyl acetate layer is dried
  4. 4
    기타evaporated
  5. 5
    기타to remove the solvent
  6. 6
    기타The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=1:1)

실험 절차

To a solution of 2-(6-chloropyrimidin-4-yloxy)ethanol (5.61 g) in dimethylformamide (60 ml) is added sodium azide (4.18 g), and the mixture is stirred at 70° C. for 20 hours. After cooling, the reaction solution is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=1:1) to give 2-(6-azidopyrimidin-4-yloxy)ethanol (1.68 g).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05728706uspto-grants-1998_03